| Identification | Back Directory | [Name]
4-BROMO-1-BROMOMETHYL-2-CHLORO-BENZENE | [CAS]
89720-77-4 | [Synonyms]
4-BROMO-1-BROMOMETHYL-2-CHLORO-BENZENE
Benzene, 4-bromo-1-(bromomethyl)-2-chloro- | [EINECS(EC#)]
827-885-3 | [Molecular Formula]
C7H5Br2Cl | [MDL Number]
MFCD15526905 | [MOL File]
89720-77-4.mol | [Molecular Weight]
284.38 |
| Hazard Information | Back Directory | [Uses]
4-Bromo-1-bromomethyl-2-chlorobenzene is used in the preparation of selective aldose reductase inhibitors. | [Synthesis]
To a solution of (4-bromo-2-chlorophenyl)methanol (2.80 g, 12.67 mmol) in dichloromethane (60.0 mL) was added sequentially carbon tetrabromide (4.41 g, 13.30 mmol) and triphenylphosphine (3.48 g, 13.30 mmol) under argon protection and at 0 °C. The reaction mixture was stirred at room temperature for 4 hours. After completion of the reaction, the mixture was concentrated under reduced pressure and the resulting crude product was purified by fast column chromatography (eluent: hexane solution of 10% ethyl acetate) to afford 2-chloro-4-bromobenzyl bromide as a colorless oil (3.59 g, 100% yield).1H NMR (400 MHz, CDCl3): δ 4.53 (s, 2H), 7.29 (d, J = 8.2 Hz. 1H), 7.39 (dd, J = 8.2, 1.9 Hz, 1H), 7.56 (d, J = 1.9 Hz, 1H). | [References]
[1] Patent: WO2004/74270, 2004, A2. Location in patent: Page 175
[2] Patent: WO2006/18725, 2006, A1. Location in patent: Page/Page column 235-236
[3] Patent: WO2008/18827, 2008, A1. Location in patent: Page/Page column 65-66
[4] Patent: WO2010/15652, 2010, A2. Location in patent: Page/Page column 68
[5] Tetrahedron Letters, 2016, vol. 57, # 3, p. 449 - 451 |
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