Benzyl Bromide → HCID 68763871, compound

Participants

Reaction Steps

5-Chloro-2-hydroxy-benzamide (1.5 g, 8.7 mmol) was dissolved in DMF (120 mL) and to the stirred solution K2CO3 (1.38 g, 10 mmol) and benzylbromide (1.71 g, 10 mmol) were added. The mixture was stirred at room temperature overnight. The suspension was concentrated in vacuo, and the residue was partitioned between water (30 mL) and Et2O (30 mL). The aqueous phase was separated and extracted with ether (20 mL×2). The combined organic phases were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate 90/10), to give 75 as a white solid (2.15 g, 95%). 1H NMR (CDCl3, 300 MHz) δ8.20 (d, J=3 Hz, 1H), 7.67 (br s, 1H), δ7.44-7.38(m, 6H), 7.99 (d, J=9 Hz, 1H), 5.85 (br s, 1H), 5.17 (s, 2H). MS (m/e) (positive FAB) 262.1 (M+H)+. m.p. 110-112° C.

Provenance & Evidence