Acetic Acid → 2-(2-Fluoro-6-nitrophenyl)ethan-1-ol

Participants

Reaction Conditions

Reaction Steps

While cooling on ice, 6.52 g (94.5 mmol) of sodium nitrite was added to 45 ml of concentrated sulfuric acid through 30 minutes. Then, 180 ml of acetic acid solution containing 14.5 g (72.9 mmol) of the compound (124) obtained in Reference Example 6 was dropped to the solution through 1.5 hours below 20° C. The solution was stirred for 20 minutes. The solution was dropped to 300 ml ethanol suspension containing 40.9 g (285.8 mmol) of cuprous oxide. The reaction solution was heated at 50° C. and was stirred for minutes. The solution was added to 1.0 l of ice/water, and 1.0 l of chloroform was added to the solution. The insoluble matter was filtered off, and the organic layer was separated. After drying over magnesium sulfate, the solvent was removed by distillation, and the residue was separated by column chromatography (silica gel 500 g, eluent solvent; chloroform) to obtain 6.22 g of the subject compound (185) in a 46% yield.

Provenance & Evidence