Benzyl Bromide → HCID 67209013, compound

Participants

Reaction Steps

To a solution of 5-(5′-bromo-2′-hydroxyphenyl)-2-adamantanone (4.57 g, 14.20 mmol) in acetone (42 mL) was added benzyl bromide (2.67 g, 15.6 mmol) followed by K2CO3 (2.65 g, 19.2 mmol). The mixture was stirred at reflux for 25.7 h under argon. Acetone was removed, and 2 N HCl (60 mL) was added. The resultant mixture was extracted with EtOAc (250 mL), and the organic layer was washed with brine and dried. After removal of solvent at reduced pressure, the residue was purified on silica gel (14% to 20% EtOAc/hexane) to give 5.48 g (94%) of 5-(2′-benzyloxy-5′-bromophenyl)-2-adamantanone as a white solid, mp 163-165° C. 1H NMR (DMSO-d6) δ 1.79-2.42 (m, 13H, AdCH and AdCH2), 5.12 (s, 2H, C6H5CH2), 7.03 (d, J=8.5 Hz, 1H, 3′-ArH), 7.21 (d, J=2.4 Hz, 1H, 4′-ArH), 7.29-7.44 ppm (m, 6H, 6′-ArH, C6H5).

Provenance & Evidence