Benzeneacetic acid, .alpha.-broMo-2-chloro-, ethyl ester synthesis

5synthesis methods

Product Name:Benzeneacetic acid, .alpha.-broMo-2-chloro-, ethyl ester
CAS Number:2856-79-3
Molecular formula:C10H10BrClO2
Molecular Weight:277.5422

40061-54-9 Synthesis

40061-54-9
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Benzeneacetic acid, .alpha.-broMo-2-chloro-, ethyl ester

2856-79-3
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Yield:2856-79-3 100%

Reaction Conditions:

with N-Bromosuccinimide;2,2'-azobis(isobutyronitrile) in tetrachloromethane; for 8 h;Heating / reflux;

Steps:

6

Ethyl 2-(2-chlorophenyl)-2-(1H-imidazol-1-yl)acetate (26)A mixture of ethyl 2-chlorophenylacetate (2.3 g, 11.60 mmol), N- bromosuccinimmide (2.3 g, 12.81 mmol) and a catalytic amount of α,α'- azobis(isobutyronitrile) in carbon tetrachloride (27.0 ml_) was heated under reflux for 8h. The reaction mixture was cooled to room temperature and the resulting suspension was filtered over cotton. The organic filtrate was washed with 1 N solution of NaOH (3 x 5 ml_), dried over Na2SO₄ and the solvent was removed. The ethyl 2-bromo-2-(2-chlorophenyl)acetate (3.2 g, 100%) thus obtained was dissolved in acetone (40 ml_) in the presence of imidazole sodium derivative (1.04 g, 11.61 mmol). The resulting yellow mixture was heated under reflux for 6h. After cooling to room temperature, H₂O (10 ml_) was added. The aqueous phase was extracted with EtOAc (3 x 30 ml_) and the organic extracts were dried over Na₂SO₄ and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (ethyl acetate) to afford 26 (1.8 g, 60%) as brownish oil. ¹H-NMR (CDCI₃, 200 MHz) δ 7.56 (s, 1 H), 7.46-7.42 (m, 1 H), 7.39-7.33 (m, 3H), 7.06 (s, 1 H), 6.98 (s, 1 H), 7.06 (s, 1 H), 4.28 (q, 2H, J = 7.0 Hz,), 1.26 (t, 3H, J = 7.0 Hz,); ESI MS m/z (M+1 )⁺ 265.

References:

WO2007/104696,2007,A1 Location in patent:Page/Page column 61-62