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

Participants

Reaction Conditions

Reaction Steps

Following the procedures described in Middleton and Bingham J. Org. Chem., 1980, 45, 2883, 500 mg portion of 7-5 (4.826 mmol) was dissolved in 25 ml of THF and cooled to 0° C. via ice bath. To this stirred solution was added 30 ml (30 mmol) of 1M Borane·THF complex dropwise over ten mintes via syringe. 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 diluted with water and concentrated in vacuo. The residue was diluted with chloroform and washed with 10% sodium carbonate. Three chloroform extractions were performed on the aqueous layer. The organic layers were combined, dried (sodium sulfate), and concentrated in vacuo to give 450 mg of a yellow oil. The oil was purified using a 30mm column, 5 inches of silica gel, and a 1:1 ethyl acetate to hexane solvent system to give 7-6 (Wade and Kheribet J. Org. Chem, 1980, 45, 5333) as a yellow oil: H1NMR CDCl3): δ 3.15 (t, 2H, 14.6 Hz), 7.4-7.49 (m, 5H).

Provenance & Evidence