Benzyl Bromide → HCID 89610023, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-(thiophen-2-ylmethyl)pyridine (H) (3.1 g, 11.52 mmol) in DMF (10 mL) was added benzyl bromide (2.16 g, 12.67 mmol) at 20-35° C. and the reaction mixture was allowed to stir at 100° C. for 3 h. Then the reaction mixture was cooled to 20-35° C., diluted with ethanol (30 mL) and NaBH4 (0.65 g, 17.28 mmol) was added slowly portionwise at 0° C. and then heated at 70-80° C. for 2 h. The reaction mixture was rotary evaporated, resultant residue was diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was rotary evaporated under vacuum to get residue which was purified by column chromatography using a mixture of 20% ethyl acetate/hexane as an eluent to get the desired compound as a light brown oily liquid (3.3 g, 67%); 1H NMR (400 MHz, DMSO-d6) δ 7.33-7.28 (m, 5H), 7.28-7.22 (m, 1H), 6.94 (dd, J=3.4, 5.4 Hz, 1H), 6.84-6.82 (m, 1H), 5.46 (s, 1H), 3.51 (s, 2H), 3.46 (s, 2H), 2.87 (s, 2H), 2.46 (t, J=5.9 Hz, 2H), 1.98 (s, 2H).

Provenance & Evidence