[Br:1]Br.[F:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)(Cl)(Cl)Cl>[F:3][C:4]1[CH:9]=[C:8]([CH2:10][Br:1])[CH:7]=[CH:6][C:5]=1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1In this instance one equivalent of Br2 was added dropwise to a refluxing solution of 2-fluoro-4-methylbiphenyl and CCl4 while being irradiated with a sunlamp. NMR analysis showed the ratio of starting material:monobromide:dibromide to be 21:67:12.
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