1-Bromo-3-chloropropane → HCID 18507150, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of hexane washed 60% sodium hydride (0.35 g, 8.6 mmol) in DMF (2 mL) at 0° C. was added a solution of (5-bromo-pyridin-2-yl)-(3-methoxy-phenyl)-acetonitrile (1.75 g, 5.76 mmol) in DMF (5 mL). The reaction mixture was stirred at 0° C. for 30 min and at room temperature for 1 h. 1-bromo-3-chloropropane (0.69 mL, 6.91 mmol) was added and the mixture was stirred at room temperature for 4 h. To the reaction mixture was added H2O (5 mL) and Et2O and the organic layer was washed with brine (5×5 mL), dried over Na2SO4 and concentrated. Purification by flash chromatography with hexanes/EtOAc (10:1) yielded 1.81 g of 2-(5-bromo-pyridin-2-yl)-5-chloro-2-(3-methoxy-phenyl)-pentanenitrile. 1HNMR (400 MHz, CDCl3) δ 8.65 (s, 1H), 7.76 (dd, 1H), 7.36 (d, 1h), 7.27-7.21 (m, 1H), 7.03 (d, 1H), 6.98 (s, 1H), 6.82 (dd, 1H), 4.77 (s, 3H), 3.55 (t, 2H), 2.79-2.70 (comp, 1H), 2.62-2.52 (comp, 1H), 1.89-1.79 (comp, 2H); MS (M+1) 378.8, 380.8.

Provenance & Evidence