Phenol → 8-Bromo-2-phenoxyquinoline

Participants

Reaction Conditions

Reaction Steps

NaH (60% w/w in mineral oil; 1.311 g, 32.8 mmol) was added to a solution of phenol (3.09 g, 32.8 mmol, Aldrich) in THF (219 ml) at 0° C.; the resulting mixture was stirred for 10 min before 8-bromo-2-chloroquinoline (178a, 5.30 g, 21.86 mmol, Biofine International, Inc., Vancouver, BC) in THF (100 ml) was added. The reaction was stirred at 0° C. for 1 h before it was warmed to RT and stirred for 3 h, then heated at reflux for 24 h. Purification by silica gel chromatography (100% hexanes to 10% EtOAc/hexanes) provided 8-bromo-2-phenoxyquinoline (178b, 41% yield) as a light yellow oil. MS (ESI, pos. ion) m/z: 300.0/302 (M+1).

Provenance & Evidence