Benzyl Bromide → HCID 67209107, compound

Participants

Reaction Steps

To a solution of 2-(1-adamantyl)-4-bromo-5-methylphenol (6.53 g, 20.34 mmol) in acetone (65 mL) was added benzyl bromide (3.48 g, 20.34 mmol) followed by K2CO3 (3.51 g, 25.43 mmol). The mixture was stirred and heated at reflux for 24 h under argon. Acetone was removed at reduced pressure, and then 2 N HCl (80 mL) was added. The mixture was extracted with EtOAc (300 mL), and the organic layer was washed with H2O and brine and dried. After removal of solvent, the residue was purified by chromatography on a silica gel using hexane to give 7.68 g (80%) of 5-(1-adamantyl)-4-benzyloxy-2-methylphenyl bromide as a white solid, mp 138-139° C. IR 2903, 2848, 1163 cm−1; 1H NMR (CDCl3) δ 1.71 (bs, 614, AdCH2), 2.02 (bs, 3H, AdCH), 2.08 (bs, 6H, AdCH2), 2.33 (s, 3H, CH3), 5.07 (s, 2H, C6H5CH2), 6.80 (s, 1H, 3-ArH), 7.33 (s, 1H, 6-ArH), 7.3-7.5 ppm (m, 5H, C6H5).

Provenance & Evidence