4-(BROMOMETHYL)-3-NITROBENZOIC ACID

2493-04-1

20782-91-6

General procedure for the synthesis of 2-(bromomethyl)-5-nitrofuran from (5-nitrofuran-2-yl)methanol: tribromoisocyanuric acid (14.05 g, 38.34 mmol, 1.5 eq.) was added to a stirred solution of triphenylphosphine (39.40 g, 150.24 mmol, 4.3 eq.) in dichloromethane (200 mL). after 30 min. (5-nitrofuran-2-yl)methanol (5 g, 34.94 mmol, 1 eq.) was added and the suspension was stirred at room temperature for 4 hours. After completion of the reaction, the precipitated cyanuric acid was filtered out and the organic layer was washed with water (4 x 100 mL), followed by brine solution. The organic layer was dried with Na2SO4, filtered and evaporated under reduced pressure. The residue obtained was treated with hexane and filtered through a short column filled with silica gel (100-200 mesh). Evaporation of hexane afforded the target product 2-(bromomethyl)-5-nitrofuran as a yellow oily liquid; Yield: 6.33 g, 84%. IR (KBr, νmax, cm-1 ): 1526 and 1345 (NO2); 1H NMR (400 MHz, CDCl3) δ 4.49 (s, 2H), 6.64 (d, J = 4.0 Hz. 1H, H3-furan), 7.28 (d, J = 4.0 Hz, 1H, H4-furan).