Ethanol → Ethyl 2-(2-bromo-6-fluorophenyl)acetate
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10]#N.S(=O)(=O)(O)[OH:13].[CH2:17]([OH:19])[CH3:18]>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10]([O:19][CH2:17][CH3:18])=[O:13]Participants
4
Procedure
A solution of 329 (3.89 g, 18.17 mmol) and concentrated sulfuric acid (35 mL) in ethanol (80 mL) was heated to reflux overnight. The mixture was allowed to cool down to room temperature, and poured into a mixture of ice/water, shaken for 15 min, and extracted with AcOEt. The extract was successively washed with water, sat. NaHCO3, water, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford title compound 330 (4.86 g, quantitative yield, contaminated) as a yellow oily liquid. LCMS: 261.0 and 263.0 (M+H)+.