To a degassed solution of 1-(2-tributylstannylphenyl)-1H-[1,2,4]triazole (300 mg, 0.7 mmol) in N,N-dimethylformamide (5 ml) was added 1,3-dibromobenzene (0.17 ml, 1.4 mmol), tetrakis(triphenylphosphine)palladium(0) (40 mg, 35 μmol), lithium chloride (293 mg, 6.9 mmol), then copper(I) iodide (13 mg, 69 μmol), and the mixture was heated at 80° C. for 5 h. The reaction was cooled to ambient temperature then poured into water (20 ml) and extracted with dichloromethane (3×20 ml). The combined organic phases were dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. Purification by chromatography on silica gel eluting with dichloromethane on a gradient of methanol (0-1%), then by preparative thin-layer chromatography on silica gel using 5% methanol in dichloromethane as eluent, gave 1-(3′-bromobiphenyl-2-yl)-1H-[1,2,4]triazole as a colourless gel: m/z (ES+) 300, 302 (M++H).
