[C:1]([C:3]1[NH:7][C:6]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=2[Cl:19])=[N:5][CH:4]=1)#[N:2].[Br:20]Br.C(OCC)(=O)C>ClC(Cl)C(Cl)Cl>[Br:20][C:4]1[N:5]=[C:6]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([C:15]([F:17])([F:16])[F:18])=[CH:10][C:9]=2[Cl:19])[NH:7][C:3]=1[C:1]#[N:2]A mixture of 5-cyano-2-(2,6-dichloro-4-trifluoromethylphenyl)imidazole (1.0 g, 0.0033 mol) and bromine (1.9 g, 0.64 ml, 0.13 mol) in 1,1,2,2-tetrachloroethane (20 ml) was stirred and heated at 90° C. for 7 hours. Ethyl acetate (50 ml) was added and the solution was washed with water (50 ml), aqueous sodium metabisulphite solution (50 ml), water (50 ml), dried over anhydrous sodium sulphate and evaporated to dryness. The solid residue was purified by chromatography on silica gel eluting with a mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.)(3:10) to give 4-bromo-5-cyano-2-(2,6-dichloro-4-trifluoromethylphenyl)imidazole (2.15 g) as a white solid m.p. 270.5°-272° C.
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