Hydrochloric Acid → HCID 59582968, compound

Participants

Reaction Conditions

Reaction Steps

Under the atmosphere of argon, 5.87 g of 10-bromobenzo[g]chrysene was placed in a flask, and 100 mL of dehydrated ether was added. After cooling the reaction solution to −40° C., 11 mL of a 1.6M hexane solution of n-butyllithium was added. The resulting solution was heated to 0° C., followed by stirring for 1 hour. The reaction solution was cooled to −60° C., and 10 mL of a dehydrated ether solution of 7.72 g of triisopropyl borate was added dropwise. The reaction solution was stirred for 5 hours while heating to room temperature. 50 mL of a 10% aqueous hydrochloric acid solution was added, followed by stirring for 1 hour. After removing an aqueous phase, and an organic phase was washed with water and saturated saline, and dried with magnesium sulfate. After filtering off magnesium sulfate, the organic phase was concentrated. The resulting solids were washed with hexane, whereby 3.18 g (yield 60%) of benzo[g]chrysene-10-boronic acid as an intended product was obtained.

Provenance & Evidence