[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[C:3]=1[CH3:10].[NH:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[CH:12]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CCOC(C)=O>[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[CH:12]1A mixture of 1-bromo-3-(bromomethyl)-2-methylbenzene (250 mg, 0.947 mmol), 1H-benzo[d]imidazole (336 mg, 2.84 mmol) and potassium carbonate (131 mg, 0.947 mmol) in acetonitrile (5 mL) was stirred at rt for 5 h, The mixture was diluted with EtOAc and filtered, and the solid was washed with EtOAc. The filtrate was washed with water, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 60:40 hexane-EtOAc to EtOAc). to provide 1-(3-bromo-2-methylbenzyl)-1H-benzo[d]imidazole as a white solid (233 mg, 82%). 1H NMR (400 MHz, chloroform-d) δ 8.14 (1 H, s), 7.68-7.78 (1 H, m), 7.56 (1 H, d, J=7.9 Hz), 7.36-7.44 (1 H, m), 7.25-7.34 (2 H, m), 7.03 (1 H, t, J=7.8 Hz), 6.82 (1 H, d, J=7.7 Hz), 5.58 (2 H, s), 2.45 (3 H, s). Mass spectrum m/z 301, 303 (M+H)+.
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