Benzyl Bromide → HCID 86701113, compound

Participants

Reaction Steps

A solution of 96 (3.3 g, 6 mmol) in DMF (40 mL) was treated with sodium hydride (830 mg, 24 mmol, 70% mineral oil dispersed) for 30 min at room temperature, followed by the addition of (bromomethyl)benzene (2.1 g, 12 mmol). After additional 1 hour at room temperature, the reaction was quenched by water (100 mL) and extracted with ethyl acetate (3×40 mL). The combined organic layer was washed with brine (5×30 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a residue, which was purified by a silica gel column, eluted with 10%-30% ethyl acetate in petroleum ether to afford 97 as a brown syrup (2.8 g, 73%); (ES, m/z) [M+H]+ 637.1; 1H NMR (300 MHz, CDCl3) δ 7.24-7.41 (m, 15H), 6.32-6.34 (d, J=6.3 Hz, 1H), 4.65-4.82 (m, 5H), 4.37-4.39 (m, 3H), 4.05-4.25 (m, 3H), 3.76-3.89 (m, 1H), 3.02 (s, 6H), 2.77-2.92 (m, 4H), 1.64-1.68 (m, 2H).

Provenance & Evidence