Glycerol → 2-(1-(7-Fluoroquinolin-6-yl)ethyl)isoindoline-1,3-dione

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Reaction Steps

A mixture of 4-bromo-3,5-difluoro-phenylamine (i) (6.0 g, 28.8 mmole), 1.82 g ferrous sulfate, 8.6 mL glycerol, 1.79 mL nitrobenzene, and 5.0 mL concentrated sulfuric acid was heated gently. After the first vigorous reaction, the mixture was boiled for five hours. Nitrobenzene was removed by distillation in vacuo. The aqueous solution was acidified with glacial acetic acid, and dark brown precipitate separated, which was purified by flash chromatography (silica gel, petroleum/ethyl acetate=12/1) to give 6-bromo-5,7-difluoroquinoline (ii) as a white solid (3.5 g, 49.8%).

Provenance & Evidence