反应详情

To a stirred solution of 5-bromo-1-(bromomethyl)-2-fluoro-3-methylbenzene (6.56 g, 23.3 mmol) in acetone (150.0 mL) was added sodium bicarbonate (2.44 g, 29.1 mmol) and water (250.0 mL). The reaction was refluxed overnight. The reaction was cooled to room temperature and extracted 3× with ethyl acetate. The organic extracts were combined and washed with brine, dried over sodium sulfate and concentrated. The resultant oil was flash chromatographed (80 g silica, 5-10% ethyl acetate/hexanes gradient) to yield 2.5 g of (5-bromo-2-fluoro-3-methylphenyl)methanol as a white solid.

1. temperatureThe reaction was refluxed overnight
2. extractionextracted 3× with ethyl acetate
3. washwashed with brine
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated
6. customchromatographed (80 g silica, 5-10% ethyl acetate/hexanes gradient)