Methane → 4-Amino-2,3-difluorophenol

Participants

Reaction Steps

At room temperature, 3.5 g (0.015 mol) of (2,3-difluoro-4-hydroxyphenyl)-phenyldiazene are dissolved in 30 ml of methanol in a 100 ml three-neck flask fitted with internal thermometer, stirrer and gas inlet tube. The flask is flushed with argon, and 1.5 g of Raney nickel and 25 μl of bis(2-hydroxyethyl) sulphide are then added. 692 ml of hydrogen (0.03 mol) are then applied at room temperature with a pressure of about 1 bar. The reaction mixture is admixed with activated charcoal, stirred for a further 15 minutes and filtered over a bed of silica gel. The solvent is distilled off and the residue is washed with n-hexane, affording 2.0 g (91.9% of theory) of 4-hydroxy-2,3-difluoroaniline.

Provenance & Evidence