Triisopropyl borate → HCID 59582968, compound

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of argon, 5.87 g of 10-bromobenzo[g]chrysene was placed in a flask. Then, 200 mL of dehydrated ether and 200 mL of dehydrated toluene were added. After cooling the reaction solution to −40° C., 11 mL of a 1.6M hexane solution of n-butyl lithium was added, and the temperature was elevated to 0° C., followed by stirring for 1 hour. After cooling the reaction solution to −60° C., 10 mL of a dehydrated ether solution of 7.72 g of triisopropyl borate was added dropwisely. The stirring was conducted for 5 hours while heating the reaction solution to room temperature. Then, 100 ml of an aqueous 10% hydrochloric solution was added, followed by stirring for 1 hour. An aqueous phase was removed and an organic phase was washed with water and saturated brine, and then dried with magnesium sulfate. After the magnesium sulfate was filtered out, the organic phase was concentrated. The resulting solids were washed with hexane, whereby 3.18 g (yield: 60%) of intended benzo[g]chrysene-10-boronic acid was obtained.

Provenance & Evidence