(2,6-Difluorophenyl)acetonitrile → 2-(2,6-Difluorophenyl)ethan-1-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 5.0 g (32.65 mmole) of 2,6-difluorophenylacetonitrile in 25 ml of anhydrous tetrahydrofuran at room temperature under nitrogen was added 33.0 ml (33.0 mmole) of 1.0 molar boranetetrahydrofuran complex by syringe. The mixture was stirred 4 hours, cooled in an ice bath, and quenched under nitrogen with a solution of 10.7 ml of concentrated hydrochloric acid in 22 ml of water. The mixture was heated to re flux, stirred I hr., and the tetrahydrofuran was removed by downward distillation. The milky white suspension was diluted with 22 ml of toluene and stirred 5 minutes longer. The layers were separated and the aqueous was extracted with 20 ml of hot toluene. The aqueous layer was cooled to 0° C., 50 ml of methylene chloride and 10 ml of 50% sodium hydroxide was added, and the layers were separated. The aqueous layer was extracted with methylene chloride (2×) and the combined organics were dried over sodium sulfate. Concentration gave 2.8 g (55%) of 2,6difluorophenethylamine as a light yellow liquid; 1H NMR (300 MHz, CDCl3) δ 7.10-7.30 (m, 1H), 6.80-7.00 (t, 2H), 2.80-3.00 (m, 2H), 2.70-2.80 (m, 2H), 1.35 (s, 2H)

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