Methanesulfonic Acid → HCID 87310593, compound

Participants

Reaction Conditions

Reaction Steps

The mixture of 4-bromophenol (3.11 g, 17.98 mmol), 5-hydroxy-2-adamantanone (2.49 g, 14.98 mmol), and MeSO3H (7 mL) was stirred with heating at 80° C. (oil-bath) for 5 h. The resulting mixture was quenched with H2O (40 mL) and filtered. The precipitate was washed several times with H2O, 5% NaHCO3, and CH2Cl2 and dried to give 3.76 g (79%) of 5-(5′-bromo-2′-hydroxyphenyl)-2-adamantanone as a white solid, mp 287-289° C. 1H NMR 8 (DMSO-d6) 1.82-2.45 (m, 13H, AdCH and AdCH2), 6.71 (d, J=8.5 Hz, 1H, 3′-ArH), 7.10 (d, J=2.4 Hz, 1H, 4′-ArH), 7.16 (dd, J=2.4 Hz, 8.5 Hz, 1H, 6′-ArH), 9.78 (s, 1H, OH).

Provenance & Evidence