Ethyl bromoacetate → (2-Bromo-4-trifluoromethyl-phenoxy)-acetic acid ethyl ester

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[OH:12].Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>CCN(C(C)C)C(C)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:5]=[CH:4][C:3]=1[O:12][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

Procedure

A solution of 2.650 g (11.000 mmol) 2-bromo-4-trifluoromethyl-phenol and 1.47 mL 13.20 mmol) ethyl bromo-acetate in 20 mL Hünig base was stirred for 5 h at 120° C. The reaction mixture was diluted with EtOAc and the org. phase was washed with water, saturated aqueous sodium bicarbonate and saturated aqueous NaCl, dried over magnesium sulphate and evaporated down i. vac. Column chromatography (silica gel, gradient dichloromethane/MeOH 100:0→19:1) yielded the product.