[CH3:1][C:2]1[O:3][CH:4]=[C:5]([C:7]([F:10])([F:9])[F:8])[CH:6]=1.[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:11][CH2:1][C:2]1[O:3][CH:4]=[C:5]([C:7]([F:10])([F:9])[F:8])[CH:6]=1A solution of 2-methyl-4-trifluoromethyl-furan (J. Heterocyclic Chemistry 1970, 7, 269-272) (340 mg, 2.26 mmol), N-bromosuccinimide (423 mg, 2.38 mmol) and azobisisobutyronitrile (19 mg, 0.11 mmol) in carbon tetrachloride (10 mL) was refluxed for 1.5 h, then allowed to cool to rt and filtered through a cotton plug. The solvent was evaporated to give 2-(bromomethyl)-4-(trifluoromethyl)furan as an orange oil (508 mg, 98%). The product was pure enough by proton NMR that no further purification was necessary. 1H NMR (400 MHz, CDCl3) δ ppm 4.46 (d, J=0.44 Hz, 2H), 6.56 (d, J=0.49 Hz, 1H), 7.77 (m, 1H).
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