[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:15]N1C(=O)CCC1=O>N(C(C)(C)C#N)=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:3][C:2]=1[F:1]A mixture of 3-fluoro-4-methylbiphenyl (6.00 g), N-bromosuccinimide (5.73 g), 2,2′-azobisisobutyronitrile (0.075 g) and carbon tetrachloride (120 ml) is refluxed by heating for five hours. The reaction solution is washed with water. The residue, which is obtained by concentrating the organic layer, is purified using silica gel column chromatography (eluate: hexane/ethyl acetate=9/1) and thus, oily 4-bromomethyl-3-fluorobiphenyl (8.30 g) is obtained. 1H-NMR (CDCl3, δ): 4.57 (2H, s), 7.30 (1H, d, J=11.0 Hz), 7.34-7.40 (2H, m), 7.45 (3H, m), 7.56 (2H, d).
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