Sodium Hydroxide → 2-Amino-5-[(3,5-difluorobenzyl)oxy]benzonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 85% sodium hydrosulfite (38.1 g, 186 mmol) in water (200 mL) was added dropwise to a mixture of 5-[(3,5-difluorobenzyl)oxy]-2-nitrobenzonitrile (9 g, 31 mmol) and tetrabutylammonium chloride (5.86 g, 21.1 mmol) in dichloromethane (200 mL) under vigorous stirring. After 2 hours, the reaction mixture was cooled at 0° C. and 2N NaOH (200 mL) was added to reach a pH value of 12. The organic phase was separated and the acqueous layer was washed with dichloromethane. Organic phases were collected and treated for 3 hours with 4M hydrochloric acid in dioxane (50 mL). The reaction mixture was washed with water, NaHCO3 saturated solution and brine. Organic phase was dried over sodium sulphate, filtered and evaporated to dryness affording 7.6 g (yield 94%) of the title compound.

Provenance & Evidence