The general procedure for the synthesis of 1-(bromomethyl)isoquinoline from 1-methylisoquinoline is as follows:
1. 1-methylisoquinoline (0.99 g, 6.91 mmol), N-bromosuccinimide (NBS, 1.35 g, 1.1 eq.), azobisisobutyronitrile (AIBN, 10 mg, catalytic amount), and carbon tetrachloride (CCl4, 1 mL) were added to a reaction flask.
2. The reaction mixture was heated to reflux for 2 hours.
3. Upon completion of the reaction, the suspended solid particles were removed by filtration and the solids were washed with a small amount of CCl4.
4. The filtrate and washings were combined and concentrated under reduced pressure to remove the solvent.
5. The crude product was purified by column chromatography (eluent: 30% ethyl acetate/hexane) to afford 1-(bromomethyl)isoquinoline (270 mg, yield: 18%) as a violet solid. 6. The structure of the product was determined by 1H-1H-quinolysis.
6. The structure of the product was confirmed by 1H-NMR (500 MHz, CDCl3): δ 8.48 (d, 1H), 8.25 (d, 1H), 7.87 (d, 1H), 7.75-7.67 (m, 2H), 7.65 (d, 1H).
