Synthesis
1. 2-Bromotoluene (20 g, 117 mmol), N-bromosuccinimide (22.0 g, 123 mmol) and azodiisobutyronitrile (1 g) were dissolved in dry carbon tetrachloride (200 mL) under nitrogen protection and heated to reflux for 16 hours.
2. After completion of the reaction, cooled to room temperature and filtered.
3. To the filtrate, imidazole (15.9 g, 234 mmol) and potassium carbonate (33 g, 234 mmol) were added and refluxed under nitrogen protection for 5 hours.
4. The completion of the reaction was monitored by LC-MS and the reaction mixture was filtered.
5. The filtrate was concentrated and the residue was dissolved in dichloromethane (100 mL) and washed with water (2 x 50 mL).
6. Separate the organic phase, dry with anhydrous sodium sulfate, filter and concentrate.
7. Purify the residue using fast silica gel column chromatography to afford 1-(2-bromobenzyl)-1H-imidazole (20 g).
