反应详情

A solution of phenol (13.3 g, 141 mmol) in dry dichloromethane (370 mL) was cooled in ice bath and treated with N,N-diisopropylethylamine (34 mL, 129 mmol) followed by dropwise addition of 2,4,5-trifluorobenzoyl chloride over a period of 15 minutes. The ice bath was removed, stirring was continued for two hours at room temperature and the solution was then transferred to a separatory funnel and the organic layer was washed successively with hydrochloric acid solution (2N, 150 mL), saturated aqueous sodium bicarbonate solution, and brine, dried over anhydrous sodium sulfate, filtered and evaporated. The residue was triturated with hexane to yield an off-white solid product upon evaporation, and the hot hexane-soluble fraction of the resulting solid product was purified on silica in portions by eluting successively with hexane, and then 0-5% ether in hexane in a gradient fashion to yield phenyl 2,4,5-trifluorobenzoate as white solid.

1. customThe ice bath was removed
2. customthe solution was then transferred to a separatory funnel
3. washthe organic layer was washed successively with hydrochloric acid solution (2N, 150 mL), saturated aqueous sodium bicarbonate solution, and brine
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. customevaporated
7. customThe residue was triturated with hexane
8. customto yield an off-white solid product
9. customupon evaporation
10. customthe hot hexane-soluble fraction of the resulting solid product was purified on silica in portions
11. washby eluting successively with hexane