1689-78-7

188290-36-0

507-19-7

1689-78-7

A dichloromethane (30 mL) solution of thiophene (12.0 g, 0.143 mol) and bromo-tert-butane (19.6 g, 0.143 mol) was slowly added dropwise to a suspension of dichloromethane (30 mL) containing aluminum trichloride (19.1 g, 0.143 mol) at -78 °C for a controlled period of 1 hour. The reaction mixture was stirred continuously at -78 °C for 2 hours, followed by slow warming to room temperature and continued stirring for 18 hours. Upon completion of the reaction, the reaction mixture was diluted with dichloromethane and washed sequentially with water, 5% sodium hydroxide solution and water. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent to give the crude product. The crude product was purified by vacuum distillation (20 mmHg) to give 10.7 g of 2-(tert-butyl)thiophene in 53% yield.