The general procedure for the synthesis of 2-bromomethyl-5-trifluoromethylfuran from 5-methyl-2-trifluoromethylfuran was as follows: to a solution of 2-methyl-5-(trifluoromethyl)furan (4 g, 26.6 mmol) in chloroform (60 mL) was added sequentially N-bromosuccinimide (5.2 g, 29.3 mmol) and 2,2'-azobis(isobutyronitrile) (220 mg 1.33 mmol). The reaction mixture was heated to reflux for 15 minutes. After completion of the reaction, the reaction solution was cooled, poured into water (200 mL) and extracted with chloroform. The organic phases were combined, washed sequentially with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure to give 2-(bromomethyl)-5-(trifluoromethyl)furan (4.79 g, 78% yield). Infrared spectrum of the product (KBr pressed sheet) νmax/cm-1 : 1738, 1688, 1599, 1559. 1H-NMR (CDCl3) δ: 4.46 (2H, s), 6.45 (1H, d, J = 3.8 Hz), 6.75 (1H, d, J = 3.8 Hz).
