Benzyl Bromide → HCID 118098735, compound

Participants

Reaction Conditions

Reaction Steps

17D (2.500 g, 8.33 mmol) and (bromomethyl)benzene (1.483 mL, 12.49 mmol) were dissolved in acetone (40 mL). Cesium carbonate (5.43 g, 16.65 mmol) was added, and the reaction mixture was stirred at 50° C. for 4 h. The reaction mixture was filtered, the filter cake was washed with acetone (3×25 mL). Organic fractions were combined, and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (0-50% EtOAc/hexanes). Fractions were combined and concentrated under reduced pressure to give 17E (2.789 g, 7.14 mmol, 86% yield) as a white solid. MS (ESI) m/z: 391.0 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 7.94 (1H, d, J=11.54 Hz), 7.77-7.90 (1H, m), 7.39 (5H, s), 5.31 (2H, br. s.), 4.25-4.50 (2H, m), 2.78 (3H, s), 1.35-1.55 (9H, m).

Provenance & Evidence