Sodium borohydride → 4-Fluoro-6-trifluoromethyl-3H-isobenzofuran-1-one

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Reaction Conditions

Reaction Steps

To a solution of 5.39 mmol 3-fluoro-2-formyl-N,N-diisopropyl-5-trifluoromethyl-benzamide in 17 ml ethanol was added portionwise 5.39 mmol sodium borohydride. The temperature was maintained at 30° C. with a water bath. The mixture was then stirred at room temperature for 50 minutes then cooled in an ice-water bath. Excess sodium borohydride was destroyed by adding HCl 2N. Ethanol was removed in vacuo. The residue was taken in 25 ml HCl 6N and refluxed at 120° C. for 2 hours. The mixture was cooled to room temperature and extracted 3 times with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a white solid (71% yield). MS (m/e): 220.2 (M+, 100%)

Provenance & Evidence