Identification | More | [Name]
2'-Bromo-4-chlorophenylacetic acid methyl ester | [CAS]
24091-92-7 | [Synonyms]
2-BROMO-4-CHLOROPHENYLACETIC ACID METHYL ESTER | [EINECS(EC#)]
200-258-5 | [Molecular Formula]
C9H8BrClO2 | [MDL Number]
MFCD06658159 | [Molecular Weight]
263.52 | [MOL File]
24091-92-7.mol |
Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of methyl 2'-bromo-4-chlorophenylacetate from methyl 4-chlorophenylacetate: Methyl 4-chlorophenylacetate (14.6 g, 79.1 mmol), N-bromosuccinimide (14.4 g, 80.7 mmol), and benzoyl peroxide (1.91 g, 7.89 mmol) were dissolved in carbon tetrachloride (100 mL) and heated to reflux for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and diluted by adding hexane (500 mL). The reaction mixture was filtered and the solvent was subsequently evaporated under vacuum. The crude product was purified by silica column chromatography (eluent: ethyl acetate/hexane, 15:85) to afford methyl 2'-bromo-4-chlorophenylacetate as a colorless oil (16.9 g, 63% yield).1H NMR (400 MHz, CDCl3) δ 3.81 (s, 3H, CH3), 5.34 (s, 1H, CH), 7.44 (dd) ), J = 60.4 Hz, J = 8.4 Hz, 4H, ArH). | [References]
[1] Tetrahedron, 2002, vol. 58, # 51, p. 10113 - 10126 [2] Patent: EP1712235, 2006, A2. Location in patent: Page/Page column 53 [3] Patent: US2004/220179, 2004, A1. Location in patent: Page 34 [4] Journal of Medicinal Chemistry, 1993, vol. 36, # 23, p. 3738 - 3742 [5] Patent: US2003/191190, 2003, A1 |
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