Benzyl Alcohol → HCID 58387590, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 60% NaH in mineral oil (1.75 equiv.) in DMF (0.5 M) was added benzyl alcohol (2.5 equiv.) dropwise. After stirring for 30 minutes, 6-bromo-4-chloroquinoline (1.0 equiv.) was added and the solution was heated in a microwave at 100° C. for 30 minutes. Upon cooling, the solution was partitioned between EtOAc and H2O. Upon separation, the organic layer was washed further with H2O (3×) and NaCl(sat.), dried over MgSO4, concentrated and triturated with hexanes to yield 4-(benzyloxy)-6-bromoquinoline (73%). LC/MS=314.0/315.9 (M+H), LC=2.89 min.

Provenance & Evidence