Benzyl Bromide → HCID 22285729, compound

Participants

Reaction Steps

To a stirred solution of the product from Step E (1.2 g, 5.2 mmol) in ethanol (20 mL) was added K2CO3 (0.86 g, 6.3 mmol) followed by benzyl bromide (0.74 mL, 6.3 mmol) at room temperature. The resultant dark solution was heated at reflux for 4 h. Solvent was evaporated, the residue was diluted with 2 N HCl (60 mL), and this solution was extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine (30 mL), dried, and evaporated to a residue which was purified by column chromatography (silica, 40% ethyl acetate in hexane) to give an oil (0.79 g, 47%): MS (ES) m/z 232 (M+); 1H NMR (CDCl3) δ 7.32 (5H, m), 6.60 (1H, s), 6.59 (1H, s), 5.29 (2H, s), 4.31 (2H, m), 4.19 (1H, m), 2.90 (2H, m), 2.11 (2H, m), 1.21 (3H, d, J=6.0 Hz).

Provenance & Evidence