Br[C:2]1[C:3]([Cl:10])=[CH:4][C:5]([Cl:9])=[C:6]([F:8])[CH:7]=1.[Cu][C:12]#[N:13].CC(CC(O)CO)C.C1(C)C(C)=CC=CC=1>[Br-].C([P+](CCCC)(CCCC)CCCC)CCC>[Cl:10][C:3]1[CH:4]=[C:5]([Cl:9])[C:6]([F:8])=[CH:7][C:2]=1[C:12]#[N:13]97.6 g (0.4 mol) of 5-bromo-2,4-dichlorofluorobenzene, 35.8 g (0.4 mol) of copper(I)cyanide, 10.0 g (0.014 mol) of trimethyl(ethoxypolyoxypropyl)ammonium chloride, 5.0 g (0.015 mol) of tetrabutylphosphonium bromide and 5.0 g (0.01 mol) of polyethylene glycol dimethyl ether 500 were introduced together with 20.0 g (0.19 mol) of xylene into a 250 ml 3-neck flask fitted with a reflux condenser and blade stirrer and azeotropically dried at up to 150° C. under reduced pressure. Amount of 2,4-dichloro-5-fluorobenzonitrile formed: after 5 hours: 19 GC area-%. after 26 hours: 75 GC area-%.
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