phenylmethanol (BnOH) to (bromomethyl)benzene (BnBr) [Reaxys, Reactions (19); 2016-03-02]

Query Query OH

1. Query

Br

Results

Date

19 reactions in Reaxys

2016-03-02 02h:12m:18s (EST)

Search as: As drawn, No salts, No mixtures

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2

H

2H

OH

2H

2H

Br

Rx-ID: 305937 View in Reaxys 1/19 Yield 91 %

Conditions & References With phosphorus tribromide Dneprovskii, A. S.; Eliseenkov, E. V.; Mil'tsov, S. A.; Journal of Organic Chemistry USSR (English Translation); vol. 18; (1982); p. 317 - 324; Zhurnal Organicheskoi Khimii; vol. 18; nb. 2; (1982); p. 365 - 373 View in Reaxys

83%

3.2 :Hydrobromic acid (33percent) was added to a flask containing phenyl-d2-methanol (2.7 g, 24.51 mmol, 1.00 equiv.).

The resulting mixture was stirred at reflux for about 1 hour, and then the mixture was cooled to ambient temperature.

Standard extractive workup with dichloromethane (50 mL) gave the title product as a brown oil (3.5 g; yield=83percent).

LC-MS: m/z=173 (MH)+; 1H NMR (300 MHz, DMSO-d6) δ: 7.20-7.50 (m, 5H).

With hydrogen bromide in dichloromethane, Time= 1h, Reflux Patent; AUSPEX PHARMACEUTICALS, INC.; US2010/143505; (2010); (A1) English View in Reaxys

80 %

With bromine, triphenylphosphine in acetonitrile, Time= 2h, T= 55 °C Bialecki, Jason; Ruzicka, Josef; Attygalle, Athula B.; Journal of Mass Spectrometry; vol. 41; nb. 9; (2006); p. 1195 - 1204 View in Reaxys

80 %

With phosphorus tribromide in dichloromethane, Time= 16h, T= 0 - 20 °C Schaefer, Mathias; Dreiocker, Frank; Budzikiewicz, Herbert; Journal of Mass Spectrometry; vol. 44; nb. 2; (2009); p. 278 - 284 View in Reaxys

76 %

With pyridine, phosphorus tribromide in diethyl ether, Time= 2h, Ambient temperature Ollis, W. David; Sutherland, Ian O.; Thebtaranonth, Yodhathai; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 1981 - 1993 View in Reaxys

74 %

With hydrogen bromide in cyclohexane, Time= 2h Wills, Max T.; Wills, Irene E.; Dollen, Lawrence Von; Butler, Barry L.; Porter, John; Anderson, Arthur G.; Journal of Organic Chemistry; vol. 45; nb. 12; (1980); p. 2489 - 2498 View in Reaxys

60 %

With sulfuric acid, hydrogen bromide in water, Time= 2h, Heating Huang; Mayer; Wiegrebe; Archiv der Pharmazie; vol. 327; nb. 11; (1994); p. 735 - 738 View in Reaxys

53.6 %

With pyridine, bromine, triphenylphosphine in acetonitrile, Time= 14h, Heating Miyashita, Akira; Hotta, Masatoshi; Saida, Yoshiko; Journal of Organometallic Chemistry; vol. 473; nb. 1-2; (1994); p. 353 - 358 View in Reaxys With Petroleum ether Letsinger; Pollart; Journal of the American Chemical Society; vol. 78; (1956); p. 6079,6084 View in Reaxys With phosphorus tribromide in benzene Biellmann, J. F.; Ducep, J. B.; Schirlin, D.; Tetrahedron; vol. 36; nb. 82; (1980); p. 1249 - 1260 View in Reaxys

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With hydrogen bromide in chloroform Vitullo, V.P.; Grabowski, J.; Sridharan, S.; Journal of the American Chemical Society; vol. 102; nb. 21; (1980); p.

6463 - 6465 View in Reaxys With hydrogen bromide in benzene, Ambient temperature Hanzlik, Robert P.; Hogberg, Kerstin; Moon, Joseph B.; Judson, Charles M.; Journal of the American Chemical Society; vol. 107; nb. 24; (1985); p. 7164 - 7167 View in Reaxys With hydrogen bromide Kingston, Eric E.; Shannon, James S.; Diakiw, Vladimir; Lacey, Michael J.; Organic Mass Spectrometry; vol. 16; nb. 10; (1981); p. 428 - 440 View in Reaxys With phosphorus tribromide in dichloromethane, Time= 3h, T= -20 - -10 °C , Yield given Hanzlik, Robert P.; Schaefer, Angela R.; Moon, Joseph B.; Judson, Charles M.; Journal of the American Chemical Society; vol. 109; nb. 16; (1987); p. 4926 - 4930 View in Reaxys With phosphorus tribromide Hill, Dale H.; Parvez, Masood A.; Sen, Ayusman; Journal of the American Chemical Society; vol. 116; nb. 7; (1994); p. 2889 - 2901 View in Reaxys With hydrogen bromide Baskir, E. G.; Maltsev, A. K.; Korolev, V. A.; Khabashesku, V. N.; Nefedov, O. M.; Russian Chemical Bulletin; vol. 42; nb. 8; (1993); p. 1438 - 1440; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 8; (1993); p. 1499 1502 View in Reaxys Li, Ang; Kindelin, Patrick J.; Klumpp, Douglas A.; Organic Letters; vol. 8; nb. 6; (2006); p. 1233 - 1236 View in Reaxys

O

OH H

H N

Br

OH

O

H

O

Rx-ID: 35173929 View in Reaxys 2/19 Yield 87 %, 3 %

Conditions & References Typical procedure for the conversion of 3-phenylpropanol into 3-phenylpropyl acetate using Ph3P/Br2/ NH4OAc General procedure: To a solution of Ph3P(OAc)2, was added 3-phenylpropanol (1 mmol, 0.137 mL). The progress of the reaction was monitored by TLC (Table 3, entry 2). After completion of the reaction (0.3 h) the reaction mixture was filtered to remove the precipitated NH4Br followed by evaporation of the solvent. Column chromatography of the crude mixture on silica gel using n-hexane/EtOAc (3:1) as the eluent gave 3-phenylpropyl acetate in 90percent yield (0.159 g).

With N-bromosuccinmide, triphenylphosphine in acetonitrile, Time= 2h, T= 20 °C , Cooling with ice Iranpoor, Nasser; Firouzabadi, Habib; Davan, Elham Etemadi; Tetrahedron Letters; vol. 54; nb. 14; (2013); p. 1813 - 1816 View in Reaxys

53 %, 40 % Typical procedure for the conversion of 3-phenylpropanol into 3-phenylpropyl acetate using Ph3P/Br2/ NH4OAc General procedure: To a solution of Ph3P(OAc)2, was added 3-phenylpropanol (1 mmol, 0.137 mL). The progress of the reaction was monitored by TLC (Table 3, entry 2). After completion of the reaction (0.3 h) the reaction mixture was filtered to remove the precipitated NH4Br followed by evaporation of the solvent. Column chromatography of the crude

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mixture on silica gel using n-hexane/EtOAc (3:1) as the eluent gave 3-phenylpropyl acetate in 90percent yield (0.159 g).

With bromine, triphenylphosphine in acetonitrile, Time= 0.7h, T= 20 °C Iranpoor, Nasser; Firouzabadi, Habib; Davan, Elham Etemadi; Tetrahedron Letters; vol. 54; nb. 14; (2013); p. 1813 - 1816 View in Reaxys

OH

Br

Rx-ID: 817410 View in Reaxys 3/19 Yield 100 %

Conditions & References With 1,1,1,2,2,2-hexamethyldisilane, pyridinium hydrobromide perbromide in chloroform, Time= 0.5h, T= 25 °C Olah, George A.; Gupta, B. G. Balaram; Malhotra, Ripudaman; Narang, Subhash C.; Journal of Organic Chemistry; vol. 45; nb. 9; (1980); p. 1638 - 1639 View in Reaxys

100 %

Step-II (Preparation of benzyl bromides) General procedure: benzyl alcohols (1 mmol) in dry benzene (15 mL) and phosphorus tribromides (0.5 mL) and stirred at room temperature to get respective benzyl bromides in quantitative yields, usual work-up.

With phosphorus tribromide in benzene, T= 20 °C Parihar, Swati; Kumar, Amit; Chaturvedi, Amit K.; Sachan, Naresh Kumar; Luqman, Suaib; Changkija, Bendangla; Manohar, Murli; Prakash, Om; Chanda; Khan, Feroz; Chanotiya; Shanker, Karuna; Dwivedi, Anila; Konwar, Rituraj; Negi, Arvind S.; Journal of Steroid Biochemistry and Molecular Biology; vol. 137; (2013); p. 332 - 344 View in Reaxys

99 %

Stage 1: With 1,2,3-Benzotriazole, thionyl chloride in dichloromethane, Time= 0.0833333h Stage 2: With potassium bromide in dichloromethane, DMFA, Time= 0.5h Bandgar, Babasaheb P.; Bettigeri, Sampada V.; Monatshefte fur Chemie; vol. 135; nb. 10; (2004); p. 1251 - 1255 View in Reaxys

98 %

With trimethylsilyl chloride, lithium bromide in acetonitrile, Time= 12h, Heating Olah, George A.; Gupta, B. G. Balaram; Malhotra, Ripudaman; Narang, Subhash C.; Journal of Organic Chemistry; vol. 45; nb. 9; (1980); p. 1638 - 1639 View in Reaxys

98 %

With DMFA, sodium bromide in dichloromethane, Time= 8h, T= 25 °C De Luca, Lidia; Giacomelli, Giampaolo; Porcheddu, Andrea; Organic Letters; vol. 4; nb. 4; (2002); p. 553 - 555 View in Reaxys

98 %

With 1,3,5-trichloro-2,4,6-triazine, sodium bromide in dichloromethane, DMFA, Time= 0.25h, T= 20 °C , chemoselective reaction Nieddu, Giammario; De Luca, Lidia; Giacomelli, Giampaolo; Synthesis; nb. 24; (2008); p. 3937 - 3940; Art.No: P08208SS View in Reaxys

98 %

With 1,1,1,2,2,2-hexamethyldisilane in chloroform, Time= 1h, Reflux Mokhtary, Masoud; Lakouraj, Moslem M.; Bulletin of the Chemical Society of Ethiopia; vol. 26; nb. 2; (2012); p. 305 - 309 View in Reaxys

98 %

With silica bromide in dichloromethane, Time= 0.05h, T= 20 °C Mohanazadeh, Farajollah; Sedrpoushan, Alireza; Zolfigol, Mohammad A.; Veisi, Hojat; Letters in Organic Chemistry; vol. 9; nb. 8; (2012); p. 598 - 603,6

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View in Reaxys 98 %

With hydrogen bromide, Time= 6h, Reagent/catalyst Islam, Md. Shahinul; Choi, Won San; Kim, Sun Ha; Han, Oc Hee; Lee, Ha-Jin; Advanced Functional Materials; vol. 25; nb. 38; (2015); p. 6061 - 6070 View in Reaxys

97 %

With thionyl bromide in toluene, Time= 14h Nakamura, Hiroyuki; Usui, Taikou; Kuroda, Hirokazu; Ryu, Ilhyong; Matsubara, Hiroshi; Yasuda, Shinji; Curran, Dennis P.; Organic Letters; vol. 5; nb. 8; (2003); p. 1167 - 1169 View in Reaxys

97 %

With Silphos, bromine in acetonitrile, Time= 0.0833333h, Heating Iranpoor, Nasser; Firouzabadi, Habib; Jamalian, Arezu; Kazemi, Foad; Tetrahedron; vol. 61; nb. 23; (2005); p.

5699 - 5704 View in Reaxys

97 %

With imidazole, iodine in dichloromethane, Time= 0.25h, T= 20 °C Anilkumar, Gopinathan; Nambu, Hisanori; Kita, Yasuyuki; Organic Process Research and Development; vol. 6; nb. 2; (2002); p. 190 - 191 View in Reaxys

95 %

With sodium bromide, Time= 0.15h, Irradiation, microwave Kad, Goverdhan L.; Singh, Vasundhara; Kaur, Kanwal Preet; Singh, Jaswinder; Tetrahedron Letters; vol. 38; nb.

6; (1997); p. 1079 - 1080 View in Reaxys

95 %

With APDPP, bromine in dichloromethane, T= 20 °C Iranpoor, Nasser; Firouzabadi, Habib; Gholinejad, Mohammad; Canadian Journal of Chemistry; vol. 84; nb. 7; (2006); p. 1006 - 1012 View in Reaxys

94 %

With 1-(2-OPPh2-propyl)-3-methylimidazolium hexafluorophosphate, bromine, T= 80 °C Iranpoor, Nasser; Firouzabadi, Habib; Azadi, Roya; Tetrahedron Letters; vol. 47; nb. 31; (2006); p. 5531 - 5534 View in Reaxys

93 %

With boron tribromide, Time= 0.5h Amrollah-Madjdabadi, A.; Pham, Tung N.; Ashby, E. C.; Synthesis; nb. 8; (1989); p. 614 - 616 View in Reaxys

93 %

With t-butyl bromide, n-pentylmethylimidazolium bromide, Time= 0.8h, sonication Ranu, Brindaban C.; Jana, Ranjan; European Journal of Organic Chemistry; nb. 4; (2005); p. 755 - 758 View in Reaxys

93 %

With ziconium(IV) oxychloride octahydrate, sodium bromide in ethanol, water, Time= 1.33333h, T= 90 °C Jafarpour, Maasoumeh; Rezaeifard, Abdolreza; Heidari, Mahdieh; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 186; nb. 7; (2011); p. 1470 - 1482 View in Reaxys

92 %

With hydrogen bromide, Time= 4h, T= 120 °C Klein, Suzane M.; Zhang, Cungen; Jiang, Yu Lin; Tetrahedron Letters; vol. 49; nb. 16; (2008); p. 2638 - 2641 View in Reaxys

90 %

With NBSacc, triphenylphosphine in dichloromethane, T= 20 °C Firouzabadi, Habib; Iranpoor, Nasser; Ebrahimzadeh, Farzaneh; Tetrahedron Letters; vol. 47; nb. 11; (2006); p.

1771 - 1775

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View in Reaxys 90 %

With TBBDA, triphenylphosphine in dichloromethane, Time= 1.5h, T= 20 °C , Reagent/catalyst De Andrade, Vitor S.C.; De Mattos, Marcio C.S.; Journal of the Brazilian Chemical Society; vol. 25; nb. 5; (2014); p.

975 - 979 View in Reaxys

89 %

With Galden HT135, phosphorus tribromide, potassium carbonate in chloroform, Time= 24h, T= 20 °C Rahman, Md. Taifur; Kamata, Naoya; Matsubara, Hiroshi; Ryu, Ilhyong; Synlett; nb. 17; (2005); p. 2664 - 2666; Art.No: U24305ST View in Reaxys

89 %

With carbon tetrabromide, sodium bromide in DMFA, Time= 3h, Irradiation, Catalytic behavior Jana, Avijit; Mondal, John; Borah, Parijat; Mondal, Sujan; Bhaumik, Asim; Zhao, Yanli; Chemical Communications; vol. 51; nb. 53; (2015); p. 10746 - 10749 View in Reaxys

89 %

General procedure for the bromination of alcohols using KBr/P2O5 General procedure: To a mixture of alcohol (1 mmol) and KBr (1.5 mmol, 0.18 g) in acetonitrile (5 mL), P2O5 (1.5 mmol, 0.23 g) was added and the reaction was stirred at room temperature for the time specified in Table 3. After reaction completion (TLC or GC), the reaction mixture was filtered and the residue washed with ethyl acetate (3 × 8 mL). The combined organic layers were washed with water (10 mL) and dried over Na2SO4. The solvent was removed under reduced pressure to afford the corresponding product. If necessary, further purification was performed by column chromatography.

With phosphorous pentoxide, potassium bromide in acetonitrile, Time= 0.416667h, T= 20 °C Khazdooz, Leila; Zarei, Amin; Aghaei, Hamidreza; Azizi, Ghobad; Gheisari, Mohammad Mehdi; Tetrahedron Letters; vol. 57; nb. 2; (2016); p. 168 - 171 View in Reaxys

88 %

With N-Bromosuccinimide, triphenylphosphine, Time= 0.00277778h, microwave irradiation Lee, Jong Chan; Hwang, Eui Yong; Synthetic Communications; vol. 34; nb. 16; (2004); p. 2959 - 2963 View in Reaxys

87 %

With phosphorus tribromide in diethyl ether Dneprovskii, A. S.; Kasatochkin, A. N.; Kondakov, D. Yu.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 5; (1988); p. 833 - 838; Zhurnal Organicheskoi Khimii; vol. 24; nb. 5; (1988); p. 923 - 929 View in Reaxys

86 %

With imidazole, bromine, triphenylphosphine in dichloromethane, T= 0 - 22 °C , Inert atmosphere Stefely, Jonathan A.; Palchaudhuri, Rahul; Miller, Patricia A.; Peterson, Rebecca J.; Moraski, Garrett C.; Hergenrother, Paul J.; Miller, Marvin J.; Journal of Medicinal Chemistry; vol. 53; nb. 8; (2010); p. 3389 - 3395 View in Reaxys

82 %

With Amberlite IRA 93 (PBr3 form) in diethyl ether, Time= 1h, Ambient temperature Cainelli, Gianfranco; Contento, Michele; Manescalchi, Francesco; Plessi, Laura; Panunzio, Mauro; Synthesis; nb. 4; (1983); p. 306 - 308 View in Reaxys

81 %

With N-Bromosuccinimide, triphenylphosphine in 1,4-dioxane, Time= 0.05h, Heating Froeyen, Paul; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 102; nb. 1-4; (1995); p. 253 - 260 View in Reaxys

80 %

With carbon tetrabromide, polystyrene-supported triphenylphosphine in chloroform, Time= 0.0833333h, T= 20 °C Hodge, Philip; Khoshdel, Ezzatollah; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); nb. 2; (1984); p. 195 - 198

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View in Reaxys 80 %

With bromine, triphenylphosphine in acetonitrile, Time= 2h, T= 55 °C Bialecki, Jason; Ruzicka, Josef; Attygalle, Athula B.; Journal of Mass Spectrometry; vol. 41; nb. 9; (2006); p. 1195 - 1204 View in Reaxys

80 %

With functionalised triphenylphosphine monolith in dichloromethane, Time= 1h, Inert atmosphere Roper, Kimberley A.; Lange, Heiko; Polyzos, Anastasios; Berry, Malcolm B.; Baxendale, Ian R.; Ley, Steven V.; Beilstein Journal of Organic Chemistry; vol. 7; (2011); p. 1648 - 1655 View in Reaxys

79 %

With boron trifluoride diethyl etherate, tetraethylammonium bromide in chloroform, Time= 4h, Heating Mandal, Arun K.; Mahajan, S. W.; Tetrahedron Letters; vol. 26; nb. 32; (1985); p. 3863 - 3866 View in Reaxys

73 %

With oxalyl dichloride, tropone, lithium bromide in dichloromethane, Time= 0.0833333h, T= 20 °C , Inert atmosphere Nguyen, Thanh V.; Bekensir, Alp; Organic Letters; vol. 16; nb. 6; (2014); p. 1720 - 1723 View in Reaxys

70 %

With tetrabutylammomium bromide, triphenylphosphine, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in dichloromethane, T= 20 °C Iranpoor; Firouzabadi; Aghapour; Vaez zadeh; Tetrahedron; vol. 58; nb. 43; (2002); p. 8689 - 8693 View in Reaxys

68 %

With toluene-4-sulfonic acid, [i-C3mim]Br in toluene, Time= 0.05h, T= 200 °C , p= 10343Torr , microwave irradiation Leadbeater, Nicholas E.; Torenius, Hanna M.; Tye, Heather; Tetrahedron; vol. 59; nb. 13; (2003); p. 2253 - 2258 View in Reaxys

60 %

With triphenylphosphine, lithium bromide, diethylazodicarboxylate in tetrahydrofuran, T= 0 °C Manna, Sukumar; Falck, J. R.; Mioskowski, Charles; Synthetic Communications; vol. 15; nb. 8; (1985); p. 663 - 668 View in Reaxys

49 %

With oxalyl dichloride, triphenylphosphineoxide, lithium bromide in chloroform, Time= 7h, T= 20 °C , Appel reaction Denton, Ross M.; An, Jie; Adeniran, Beatrice; Blake, Alexander J.; Lewis, William; Poulton, Andrew M.; Journal of Organic Chemistry; vol. 76; nb. 16; (2011); p. 6749 - 6767 View in Reaxys With hydrogen bromide Kekule; Justus Liebigs Annalen der Chemie; vol. 137; (1866); p. 167 View in Reaxys With hydrogen bromide Norris; American Chemical Journal; vol. 38; (1907); p. 640 View in Reaxys With hydrogen bromide in diethyl ether, 1.) -30 deg C, 5 min; 2.) room temp., 1 h, Yield given Bilger, Christine; Royer, Rene; Demerseman, Pierre; Synthesis; nb. 11; (1988); p. 902 - 904 View in Reaxys With carbon tetrabromide, 1,10-phenanthroline monohydrate, iron, copper, copper(I) bromide in DMFA, Time= 1.5h, Ambient temperature, Yield given Leonel; Paugam; Nedelec; Journal of Organic Chemistry; vol. 62; nb. 20; (1997); p. 7061 - 7064 View in Reaxys

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98 % Chro- With triethylsilane, palladium dichloride, 1,2-dibromomethane, Time= 1h, T= 25 °C mat.

Ferreri; Costantino; Chatgilialoglu; Boukherroub; Manuel; Journal of Organometallic Chemistry; vol. 554; nb. 2; (1998); p. 135 - 137 View in Reaxys With carbon tetrabromide, polymer-bound triphenylphosphine in dichloromethane Caldarelli, Marina; Habermann, Joerg; Ley, Steven V.; Journal of the Chemical Society - Perkin Transactions 1; nb.

2; (1999); p. 107 - 110 View in Reaxys With hydrogen bromide in benzene, Time= 1h, T= 78 °C Lu; Cai; Fang; Zhou; Liu; Wu, Longmin M.; Pharmazie; vol. 57; nb. 7; (2002); p. 474 - 478 View in Reaxys With phosphorus tribromide in dichloromethane Nabil Aboul-Enein; El-Azzounya; Maklad; Attia; Wiese; Scientia Pharmaceutica; vol. 69; nb. 4; (2001); p. 329 - 350 View in Reaxys With PPh3-containing cross-linked polystyrene, bromine in dichloromethane, Time= 0.166667h, T= 20 °C Choi, Matthew Kwok Wai; He, Helen Song; Toy, Patrick H.; Journal of Organic Chemistry; vol. 68; nb. 25; (2003); p. 9831 - 9834 View in Reaxys Reaction Steps: 2 1: 74 percent / pyridine 2: 80 percent / trimethylsilyl bromide / IBr / 0.5 h / Ambient temperature With Bromotrimethylsilane, Iodine bromide in pyridine Friedrich, Edwin C.; DeLucca, George; Journal of Organic Chemistry; vol. 48; nb. 10; (1983); p. 1678 - 1682 View in Reaxys Reaction Steps: 2 2: 63 percent / CuBr2 / acetonitrile / 5.7 h / Ambient temperature With copper(ll) bromide in acetonitrile Cristol, Stanley J.; Seapy, Dave G.; Journal of Organic Chemistry; vol. 47; nb. 1; (1982); p. 132 - 136 View in Reaxys Reaction Steps: 2 2: dibutyl ether With dibutyl ether Fuson; Bottorff; Speck; Journal of the American Chemical Society; vol. 64; (1942); p. 1450; Journal of the American Chemical Society; vol. 66; (1944); p. 2135 View in Reaxys Reaction Steps: 2 1: sodium benzylate / 150 °C 2: bromine With anhydrous sodium benzoate, bromine Lachman; Journal of the American Chemical Society; vol. 45; (1923); p. 2359 View in Reaxys Reaction Steps: 2 1: sodium benzylate / 150 °C 2: bromine With anhydrous sodium benzoate, bromine Lachman; Journal of the American Chemical Society; vol. 45; (1923); p. 2359 View in Reaxys

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98 % Spectr.

With triphenylphosphine in dichloromethane, Time= 0.25h, T= 20 °C Tongkate, Pratoomrat; Pluempanupat, Wanchai; Chavasiri, Warinthorn; Tetrahedron Letters; vol. 49; nb. 7; (2008); p. 1146 - 1148 View in Reaxys With phosphorus tribromide in tetrahydrofuran, Time= 0.0833333h, T= 20 °C , UV-irradiation Min, Kyoung-Ik; Lee, Tae-Ho; Park, Chan Pil; Wu, Zhi-Yong; Girault, Hubert H.; Ryu, Ilhyong; Fukuyama, Takahide; Mukai, Yu; Kim, Dong-Pyo; Angewandte Chemie - International Edition; vol. 49; nb. 39; (2010); p. 7063 7067 View in Reaxys 3. General procedure for the synthesis of benzyl bromides A mixture of alcohol (1.2 mmol) and triphenylphosphine (1.8 mmol) was stirred in dry acetonitrile (6 mL) for 15 min.

Hexabromoacetone (0.6 mmol) was added and the stirring continued at 40° under a nitrogen atmosphere. Conversion of the alcohol into the bromide was followed by 1H NMR analysis on a sample previously quenched with cold water.

With 1,1,1,3,3,3-hexabromoacetone, triphenylphosphine in acetonitrile, T= 20 °C , Inert atmosphere Joseph, Kara M.; Larraza-Sanchez, Isabel; Tetrahedron Letters; vol. 52; nb. 1; (2011); p. 13 - 16 View in Reaxys With phosphorus tribromide in dichloromethane, Time= 1.08333h, T= 0 - 20 °C , Inert atmosphere Greger, Jessica G.; Yoon-Miller, Sarah J. P.; Bechtold, Nathan R.; Flewelling, Scott A.; MacDonald, Jacob P.; Downey, Catherine R.; Cohen, Eric A.; Pelkey, Erin T.; Journal of Organic Chemistry; vol. 76; nb. 20; (2011); p.

8203 - 8214 View in Reaxys General procedure for the preparation of 4-aminomethyl-3-(substituted benzyloxyimino)pyrrolidine dimesylates (8a-w) General procedure: To a solution of phenylmethanols 5a-w (5 mmol) dissolved in methylene chloride (50 mL) in an icewater bath was added phosphorus tribromide (5.5 mmol), and the mixture was stirred at the same temperature for 30 min. The mixture was washed with cool water, dried over anhydrous Na2SO4 and concentrated under reduced pressure to yield (bromomethyl)benzenes 6aew as offwhite solids or light yellow oils With phosphorus tribromide in dichloromethane, Time= 0.5h, T= 0 °C Feng, Lianshun; Lv, Kai; Liu, Mingliang; Wang, Shuo; Zhao, Jing; You, Xuefu; Li, Sujie; Cao, Jue; Guo, Huiyuan; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 125 - 136 View in Reaxys Reaction Steps: 2 1: pyridine / 20 °C 2: [1,3-butylmethylimidazolium]Br / 1 h / 50 °C / |Inert atmosphere; |Green chemistry With pyridine, [1,3-butylmethylimidazolium]Br Liu, Yajun; Xu, Yongnan; Jung, Sun Ho; Chae, Junghyun; Synlett; vol. 23; nb. 18; (2012); p. 2692 - 2698,7 View in Reaxys Liu, Yajun; Xu, Yongnan; Jung, Sun Ho; Chae, Junghyun; Synlett; vol. 23; nb. 18; (2012); p. 2692 - 2698 View in Reaxys With phosphorus tribromide in dichloromethane, Time= 1h, T= 20 °C Tummatorn, Jumreang; Thongsornkleeb, Charnsak; Ruchirawat, Somsak; Gettongsong, Tanita; Organic and Biomolecular Chemistry; vol. 11; nb. 9; (2013); p. 1463 - 1467 View in Reaxys With hydrogen bromide in dichloromethane, T= 20 °C , Reagent/catalyst Zhang, Qiao; Shu, Xing-Zhong; Lucas, J. Matthew; Toste, F. Dean; Somorjai, Gabor A.; Alivisatos, A. Paul; Nano Letters; vol. 14; nb. 1; (2014); p. 379 - 383 View in Reaxys With phosphorus tribromide in dichloromethane, Time= 0.5h, T= 0 °C

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Mao, Jiangang; Zhang, Shuo-Qing; Shi, Bing-Feng; Bao, Weiliang; Chemical Communications; vol. 50; nb. 28; (2014); p. 3692 - 3694 View in Reaxys With N-Bromosuccinimide, triphenylphosphine in dichloromethane, Time= 3h, T= 0 - 20 °C Bedford, Robin B.; Brenner, Peter B.; Carter, Emma; Gallagher, Timothy; Murphy, Damien M.; Pye, Dominic R.; Organometallics; vol. 33; nb. 21; (2014); p. 5940 - 5943 View in Reaxys With phosphorus tribromide in diethyl ether, Time= 2h, T= 20 °C Shu, Chao; Wang, Yong-Heng; Zhou, Bo; Li, Xin-Ling; Ping, Yi-Fan; Lu, Xin; Ye, Long-Wu; Journal of the American Chemical Society; vol. 137; nb. 30; (2015); p. 9567 - 9570 View in Reaxys With boron tribromide in dichloromethane Wilhelm, Anke; Kendrekar, Pravin; Noreljaleel, Anwar E. M.; Abay, Efrem T.; Bonnet, Susan L.; Wiesner, Lubbe; De Kock, Carmen; Swart, Kenneth J.; Van Der Westhuizen, Jan Hendrik; Journal of Natural Products; vol. 78; nb.

8; (2015); p. 1848 - 1858 View in Reaxys With phosphorus tribromide, Inert atmosphere Wang, Sunewang Rixin; Radosevich, Alexander T.; Organic Letters; vol. 17; nb. 15; (2015); p. 3810 - 3813 View in Reaxys With phosphorus tribromide in dichloromethane, Time= 2h, T= 20 °C Hu, Wei-Ping; Cao, Guo-Dong; Zhu, Jin-Hua; Li, Jia-Zhong; Liu, Xiu-Hua; RSC Advances; vol. 5; nb. 100; (2015); p. 82153 - 82158 View in Reaxys B] Synthesis of benzyl bromides: General procedure: Benzyl alcohols (1 equiv) were taken in RBF and dichloromethane as a solvent. This reaction allowed to stir below 5 °C, then added drop by drop phosphorus tribromide (PBr3) (1 equiv). The progress of the reaction was monitored by TLC using ethyl acetate: hexane as a solvent system. After completion of the reaction, the reaction mass was poured on crushed ice. Ethyl acetate was added to the mixture and the organic layer was separated. The aqueous layer was extracted with 3 x 10 mL of ethyl acetate and the combined organic layers were dried over MgSO4. Solvent was removed under reduced pressure, and the benzyl bromides were sufficiently pure to use without further work up.

With phosphorus tribromide in dichloromethane, Time= 0.5h, T= 0 - 5 °C Shaikh, Mubarak H.; Subhedar, Dnyaneshwar D.; Arkile, Manisha; Khedkar, Vijay M.; Jadhav, Nandadeep; Sarkar, Dhiman; Shingate, Bapurao B.; Bioorganic and Medicinal Chemistry Letters; vol. 26; nb. 2; (2016); p. 561 - 569 View in Reaxys

H OH 2H

2H

Br

Rx-ID: 2061601 View in Reaxys 4/19 Yield 90 %

Conditions & References With phosphorus tribromide, Time= 1.5h, T= 110 °C Kim, Jong-Man; Bogdan, Michael A.; Mariano, Patrick S.; Journal of the American Chemical Society; vol. 115; nb.

23; (1993); p. 10591 - 10595 View in Reaxys

3g

With hydrogen bromide in benzene, Time= 0.166667h, Ambient temperature Hanzlik, Robert P.; Hogberg, Kerstin; Moon, Joseph B.; Judson, Charles M.; Journal of the American Chemical Society; vol. 107; nb. 24; (1985); p. 7164 - 7167

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View in Reaxys With phosphorus tribromide Hill, Dale H.; Parvez, Masood A.; Sen, Ayusman; Journal of the American Chemical Society; vol. 116; nb. 7; (1994); p. 2889 - 2901 View in Reaxys 2

2H

H

2

2H

H OH

2H

Br 2H

2H

2H 2H

2H

Rx-ID: 2117816 View in Reaxys 5/19 Yield

Conditions & References

80 %

With bromine, triphenylphosphine in acetonitrile, T= 55 °C Bialecki, Jason; Ruzicka, Josef; Attygalle, Athula B.; Journal of Mass Spectrometry; vol. 41; nb. 9; (2006); p. 1195 - 1204 View in Reaxys

76 %

With bromine, triphenylphosphine in dichloromethane, Time= 3h, T= 0 °C Thiel, Verena; Brinkhoff, Thorsten; Dickschat, Jeroen S.; Wickel, Susanne; Grunenberg, Joerg; Wagner-Doebler, Irene; Simon, Meinhard; Schulz, Stefan; Organic and Biomolecular Chemistry; vol. 8; nb. 1; (2010); p. 234 246 View in Reaxys With hydrogen bromide Kingston, Eric E.; Shannon, James S.; Diakiw, Vladimir; Lacey, Michael J.; Organic Mass Spectrometry; vol. 16; nb. 10; (1981); p. 428 - 440 View in Reaxys H

H

13C 2

13C 2

OH

Br

Rx-ID: 2034616 View in Reaxys 6/19 Yield 89.8 %

Conditions & References With hydrogen bromide, Time= 1h, Heating Hart, Lionel S.; Waddington, Catherine R.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1985); p. 1607 - 1612 View in Reaxys

87 %

With hydrogen bromide in Petroleum ether, Time= 2h Franke, Wilfried; Schwarz, Helmut; Thies, Helga; Chandrasekhar, Jayaraman; Raque' Schleyer, Paul von; et al.; Chemische Berichte; vol. 114; nb. 8; (1981); p. 2808 - 2824 View in Reaxys

65 %

With phosphorus tribromide in diethyl ether, Time= 20h, Ambient temperature Takatori, Kazuhiko; Nishihara, Mikiko; Nishiyama, Yukie; Kajiwara, Masahiro; Tetrahedron; vol. 54; nb. 52; (1998); p. 15861 - 15869 View in Reaxys With carbon tetrabromide, triphenylphosphine Wooley, Karen L.; Klug, Christopher A.; Tasaki, Kenzabu; Schaefer, Jacob; Journal of the American Chemical Society; vol. 119; nb. 1; (1997); p. 53 - 58 View in Reaxys

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H

H

14C 2

14C 2

Br

OH

Rx-ID: 2062991 View in Reaxys 7/19 Yield

Conditions & References With hydrogen bromide Miller, David J.; Subramanian, Rm.; Saunders, William H.; Journal of the American Chemical Society; vol. 103; nb.

12; (1981); p. 3519 - 3522 View in Reaxys

284 mg

With sulfuric acid, hydrogen bromide, Substitution Koltai; Alexin; Rutkai; Toth-Sarudy; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 41; nb. 11; (1998); p. 977 - 982 View in Reaxys With carbon tetrabromide, triphenylphosphine in dichloromethane, Time= 4h, T= 20 °C , Inert atmosphere Zhang, Yinsheng; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 55; nb. 11; (2012); p. 419 - 422 View in Reaxys

Br

OH

H O

Rx-ID: 11044833 View in Reaxys 8/19 Yield

Conditions & References

34 %, 60 % With N-bromosuccinmide, water in 1,4-dioxane, Time= 1h, T= 70 °C Adimurthy, Subbarayappa; Patoliya, Paresh U.; Synthetic Communications; vol. 37; nb. 9; (2007); p. 1571 - 1577 View in Reaxys

OH

Br

BeCl2

alcoholic potash Rx-ID: 19757058 View in Reaxys 9/19

Yield

Conditions & References Reaction Steps: 2 1: 95 percent / CH2Cl2 / 0.5 h / 0 °C 2: 79 percent / CaBr2 / dimethylsulfoxide / 3 h / Ambient temperature With CaBr2 in dichloromethane, dimethyl sulfoxide Altamura, Maria; Perrotta, Enzo; Journal of Organic Chemistry; vol. 58; nb. 1; (1993); p. 272 - 274 View in Reaxys Reaction Steps: 2 1: 95 percent / SnCl4 / 1 h 2: 89 percent / BBr3 / 0.25 h With boron tribromide, tin(IV) chloride Amrollah-Madjdabadi, A.; Pham, Tung N.; Ashby, E. C.; Synthesis; nb. 8; (1989); p. 614 - 616 View in Reaxys

H OH 2H

Br

2H

H

Rx-ID: 362688 View in Reaxys 10/19

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Yield

Conditions & References With phosphorus tribromide Streitwieser; Wolfe; Journal of the American Chemical Society; vol. 79; (1957); p. 903,906; Journal of the American Chemical Society; vol. 81; (1959); p. 4912,4914 View in Reaxys O OH

Br

O

H O

Rx-ID: 9815636 View in Reaxys 11/19 Yield

Conditions & References With 2,2,6,6-tetramethyl-piperidine-N-oxyl, air, 1,3-dibromo-5,5-dimethyl-hydantoin, sodium nitrite in dichloromethane, Time= 1h, p= 3000.24Torr , Heating, Product distribution, Further Variations: Solvents, Pressures, Reagents, reaction times Liu, Renhua; Dong, Chunyan; Liang, Xinmiao; Wang, Xiujuan; Hu, Xinquan; Journal of Organic Chemistry; vol.

70; nb. 2; (2005); p. 729 - 731 View in Reaxys

H N

OH

H N

Br

O

Rx-ID: 3840140 View in Reaxys 12/19 Yield

Conditions & References With trifluorormethanesulfonic acid, tetrabutylammomium bromide, copper(l) chloride, diisopropyl-carbodiimide, 1.) 6 days, room temperature, 2.) dichloromethane, 25 deg C, 26 h, Yield given. Multistep reaction Collingwood, Stephen P; Davies, Alan P; Golding, Bernard T; Tetrahedron Letters; vol. 28; nb. 38; (1987); p. 4445 - 4448 View in Reaxys 2H

2H

OH 2H

Br 2H

2H

2H

Rx-ID: 2141743 View in Reaxys 13/19 Yield

Conditions & References With hydrogen bromide Kingston, Eric E.; Shannon, James S.; Diakiw, Vladimir; Lacey, Michael J.; Organic Mass Spectrometry; vol. 16; nb. 10; (1981); p. 428 - 440 View in Reaxys

OH

O

Br

H O

Rx-ID: 9900408 View in Reaxys 14/19 Yield

Conditions & References With bromine, triethyl phosphite, Time= 3h Iranpoor, Nasser; Firouzabadi, Habib; Jamalian, Arezu; Kazemi, Foad; Tetrahedron; vol. 61; nb. 23; (2005); p.

5699 - 5704 View in Reaxys

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Br

OH

P

Br

N

Rx-ID: 817305 View in Reaxys 15/19 Yield

Conditions & References With benzene Horner et al.; Justus Liebigs Annalen der Chemie; vol. 626; (1959); p. 26,33 View in Reaxys

Br

OH

P

Br

Br

Rx-ID: 817354 View in Reaxys 16/19 Yield

Conditions & References With tetrachloromethane Horner et al.; Justus Liebigs Annalen der Chemie; vol. 626; (1959); p. 26,33 View in Reaxys

Br

H OH

Br

2H

P

Br

2H

H

Br

Rx-ID: 7912263 View in Reaxys 17/19 Yield

Conditions & References Streitwieser; Wolfe; Journal of the American Chemical Society; vol. 79; (1957); p. 903,906; Journal of the American Chemical Society; vol. 81; (1959); p. 4912,4914 View in Reaxys

O N

Br

OH

N

P

N O

O N

N

Br P

NH

O

O

Rx-ID: 3409600 View in Reaxys 18/19 Yield

Conditions & References

91 % Chro- in tetrahydrofuran, Ambient temperature, 1) 0 deg C, 2) CH3Br, room temperature, 6 h; prototype reaction, oth. alcohols, mat. oth. phosphine, Product distribution Oshikawa, Tatsuo; Yamashita, Mitsuji; Bulletin of the Chemical Society of Japan; vol. 57; nb. 9; (1984); p. 2675 2676 View in Reaxys

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OH

Br

Br

H

Rx-ID: 5818101 View in Reaxys 19/19 Yield

Conditions & References Norris; American Chemical Journal; vol. 38; (1907); p. 640 View in Reaxys Kekule; Justus Liebigs Annalen der Chemie; vol. 137; (1866); p. 167 View in Reaxys

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