Hydrochloric Acid → HCID 59582968, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 5.87 g of 10-bromobenzo[g]chrysene in an argon atmosphere. 100 mL of dehydrated diethyl ether was then added to the flask. After cooling the reaction solution to −40° C., 11 mL of a 1.6 M hexane solution of n-butyllithium was added to the reaction solution. The mixture was heated to 0° C., and stirred for 1 hour. After cooling the reaction solution to −60° C., a dehydrated diethyl ether (10 mL) solution of 7.72 g of triisopropyl borate was added dropwise to the reaction solution. The reaction solution was stirred at room temperature for 5 hours. After the addition of 50 mL of a 10% hydrochloric acid aqueous solution, the mixture was stirred for 1 hour. After removing the aqueous phase, the organic phase was washed with water and a saturated sodium chloride solution, and dried over magnesium sulfate. After removing magnesium sulfate by filtration, the organic phase was concentrated. The resulting solid was washed with hexane to obtain 3.18 g of the target benzo[g]chrysene-10-boronic acid (yield: 60%).

Provenance & Evidence