Benzyl Bromide → HCID 58292737, compound

Participants

Reaction Steps

To a mixture of (1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.2 g, 0.8 mmol) in anhydrous DMF (3 mL) was added sodium hydride (0.08 g, 1.6 mmol). After stirring for 15 minutes bromomethyl-benzene (0.274 g, 1.6 mmol) was added and the resulting mixture stirred at room temperature for 4 hours then quenched with crushed ice. The pH was adjusted to 4 with 6M HCl and the mixture extracted with EtOAc. The organic extracts were washed with water, brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by Biotage (5-60% EtOAc in hexane) to give 6-benzyloxy-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.2 g, 73%). 1H NMR 400 MHz (DMSO-d6) δ 9.15 (s, 1H), 7.45-7.31 (m, 5H), 7.11 (d, J=2.0 Hz, 1H), 6.94 (d, =2.0 Hz, 1H), 5.44 (dd, J=9.2, 2.4 Hz, 1H), 5.10 (s, 2H), 4.05 (q, J=7.2 Hz, 2H), 3.08 (dd, J=15.2, 2.4 Hz, 1H), 2.26 (s, 3H), 2.21 (m, 1H), 1.08 (t, 3H).

Provenance & Evidence