Methanol → 3-Ethyl-2-nitro-4-trifluoroacetamidophenol

Participants

Reaction Steps

A solution of 3-ethyl-2-nitro-4-trifluoroacetamidoanisole (19.3 mmol) in dry methylene chloride (250 mL) at -78° C. under nitrogen atmosphere is treated dropwise with a solution of boron tribromide (96.9 mmol) in dry methylene chloride (50 mL). After complete addition, the mixture is allowed to warm to room temperature and stirring is maintained for one hour. The mixture is cooled to -78° C. and methanol (100 mL) is added dropwise. After complete addition, the solution is allowed to warm to room temperature. The reaction mixture is distributed between water (100 mL) and methylene chloride (200 mL). The methylene chloride layer is dried over magnesium sulfate and concentrated under reduced pressure to yield 3-ethyl-2-nitro-4-trifluoroacetamidophenol.

Provenance & Evidence