2,2-Difluoro-2-phenylacetamide → 2,2-Difluoro-2-phenylethylamine

Participants

Reaction Conditions

Reaction Steps

2,2-Difluoro-2-phenylacetamide (2-9) (7.8 g, 45.03 mmol) was dissolved in THF (200 mL) and cooled to 0° C. with an ice bath. To this stirred solution was added 1M borane-tetrahydrofuran complex (315.2 mL, 315.2 mmol) dropwise over 15 minutes using a dropping funnel. The reaction mixture was aged until the ice bath expired. Upon expiration of the ice bath, the reaction mixture was heated to 70° C. overnight. The reaction mixture was allowed to cool to ambient temperature, then was quenched by the careful dropwise addition of water (100 mL). The mixture was concentrated in vacuo. The residue was diluted with dichloromethane (100 mL) and washed with 10% sodium carbonate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The crude residue was purified by flash chromatography (ethyl acetate/hexane) (1:1 to 1:0 gradient) to afford the title compound (6.2 g, 86%) as a yellow oil. 1H-NMR (CDCl3): δ 3.15 (t, J=14.0 Hz, 2H), 7.41-7.45 (m, 5H).

Provenance & Evidence