| Identification | Back Directory | [Name]
1-broMo-2,3-bis(broMoMethyl)benzene | [CAS]
127168-82-5 | [Synonyms]
2,3-BIS(BROMOMETHYL)BROMOBENZENE
1-broMo-2,3-bis(broMoMethyl)benzene
Benzene, 1-broMo-2,3-bis(broMoMethyl)- | [Molecular Formula]
C8H7Br3 | [MOL File]
127168-82-5.mol | [Molecular Weight]
342.85 |
| Hazard Information | Back Directory | [Synthesis]
The general procedure for the synthesis of 1-bromo-2,3-bis(bromomethyl)benzene from 1-bromo-2,3-dimethylbenzene is as follows:
General method (a): 1-bromo-2,3-dimethylbenzene (10 mmol) was mixed with a solution of finely pulverized N-bromosuccinimide (NBS, 3.68 g, 21 mmol, 2.1 equiv) in carbon tetrachloride (CCl4, 40-80 mL). The reaction was irradiated with an HPK125 mercury lamp for 1-2 h while maintaining stirring (the progress of the reaction was monitored by thin layer chromatography (TLC) or 1H NMR). Upon completion of the reaction, the reaction mixture was diluted with dichloromethane (CH2Cl2), washed sequentially with water or 2N aqueous ammonium chloride (NH4Cl), and then dried with magnesium sulfate (MgSO4). The solvent was removed by evaporation to give the product 1-bromo-2,3-bis(bromomethyl)benzene (5b-e, h), which can be used in subsequent steps without further purification. | [References]
[1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 18, p. 5716 - 5733
[2] Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 11, p. 3067 - 3075
[3] Phytochemistry, 2007, vol. 68, # 4, p. 407 - 415
[4] Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 7804 - 7815
[5] Tetrahedron Letters, 2007, vol. 48, # 19, p. 3379 - 3383 |
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