Hydrochloric Acid → HCID 90052104, compound

Participants

Reaction Steps

To a suspension of zinc (962 mg) in tetrahydrofuran (25 mL), trimethylsilyl chloride (1 drop) and ethyl bromodifluoroacetate (2.2 mL) were added at room temperature, and the mixture was stirred for 5 minutes under reflux by heating. To the reaction mixture, 3-nitrobenzaldehyde (695 mg) was added, and the mixture was stirred for 30 minutes under reflux by heating. The reaction mixture was cooled to room temperature, and then ethyl acetate and 1.0 mol/L aqueous hydrochloric acid were added to the mixture. The organic layer was separated, washed successively with 1.0 mol/L aqueous hydrochloric acid and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 60% hexane in ethyl acetate) to obtain ethyl 2,2-difluoro-3-hydroxy-3-(3-nitrophenyl)propanoate (C29, 1.02 g).

Provenance & Evidence