Methanesulfonic Acid → HCID 85724205, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-2-methoxyphenol (2.00 g, 9.85 mmol), 1-adamantanol (1.50 g, 9.85 mmol), and MeSO3H (0.8 mL) in CH2Cl2 (8 mL) was stirred with heating at 54° C. (oil-bath) for 18.3 h. The resulting solution was quenched with H2O (30 mL) and extracted with EtOAc (120 mL). The extract was washed with 5% NaHCO3 and brine and dried. The residue obtained on concentration was purified on silica gel (4% EtOAc/hexane) to give 2.5 g (76%) of 2-(1-adamantyl)-4-bromo-6-methoxyphenol as a white solid, mp 157-159° C. IR 3510, 2903, 2850, 1413, 1217 cm−1; 1H NMR δ (CDCl3) 1.76 (bs, 6H, AdCH2), 2.07 (bs, 9H, AdCH and AdCH2), 3.87 (s, 3H, OCH3), 5.90 (s, 1H, OH), 6.86 (d, J=2.4 Hz, 1H, 5-ArH), 6.95 ppm (d, J=2.4 Hz, 1H, 3-ArH).

Provenance & Evidence