Benzyl Bromide → HCID 67209097, compound

Participants

Reaction Steps

To a solution of 2-(1-adamantyl)-4-bromo-6-methoxyphenol (3.30 g, 79.78 mmol) in acetone (32 mL) was added benzyl bromide (1.72 g, 10.07 mmol) followed by K2CO3 (1.69 g, 12.2 mmol). This mixture was stirred and heated at reflux temperature for 20.75 h under argon. Acetone was removed at reduced pressure, and 2 N HCl (30 mL) was added. The mixture was extracted with EtOAc (150 mL), and the organic layer was washed with brine and dried. After removal of solvent at reduced pressure, the residue was crystallized (MeOH) to give 3.99 g (95%) of 3-(1-adamantyl)-4-benzyloxy-5-methoxyphenyl bromide as a white solid, mp 89-91° C. IR 2901, 2847, 1444, 1201 cm−1; 1H NMR (CDCl3) δ 1.67 (m, 6H, AdCH2), 2.00 (bs, 3H, AdCH), 2.05 (bs, 6H, AdCH2), 3.85 (s, 3H, OCH3), 5.07 (s, 2H, C6H5CH2), 6.96 (d, J=2.3 Hz, 1H, 6-ArH), 7.01 (d, J=2.3 Hz, 1H, 2-ArH), 7.30-7.52 ppm (m, 5H, C6H5).

Provenance & Evidence