Benzyl Bromide → HCID 14103203, compound

Participants

Reaction Steps

A solution of 126 (5 g, 26 mmol) in DMF (50 mL) was treated with sodium hydride (1.1 g, 32 mmol, 70% dispersed in mineral oil) for 30 minutes at room temperature, followed by addition of BnBr (6.7 g, 39 mmol). After additional 1 hour, the reaction was quenched by water (200 mL) and extracted with ethyl acetate (4×50 mL). The combined organic layer was washed with brine (3×50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluted with 10%-20% ethyl acetate in petroleum ether to afford 127 as a white solid (4.8 g, 65%). (ES, m/z) [M+H]+ 282.0; 1H NMR (300 MHz, CDCl3) δ 7.85-7.88 (m, 2H), 7.71-7.74 (m, 2H), 7.25-7.31 (m, 5H), 4.55 (s, 2H), 3.95 (t, J=6.0 Hz, 2H), 3.74 (t, J=6.0 Hz, 2H).

Provenance & Evidence