2-Fluoro-4-nitroanisole → 3-Fluoro-4-methoxyaniline

Participants

Reaction Steps

To a cold (5°), stirred solution of 776 g. (3.44 mol) of stannous chloride dihydrate in 1500 mL of concentrated hydrochloric acid was added, dropwise, a solution of 147 g. (0.861 mol) of 2-fluoro-4-nitroanisole in 3.0 L of ethanol at such a rate that the temperature of the reaction mixture did not exceed 23°. The suspension was stirred for 6 hours at room temperature. The ethanol was removed in vacuo at temperatures below 45°, and the residue was diluted with 3.0 L of water then basified with 1.0 L of 50% sodium hydroxide. The temperature of the mixture was maintained below 23° during the dropwise addition of the base.

Provenance & Evidence