Hexane → 4-Cyanophenylboronic acid

Participants

Reaction Conditions

Reaction Steps

4-Bromobenzonitrile (20 g, 0.1099 m) was dissolved in tetrahydrofuran (240 mls) and hexane (80 mls) and the mixture treated with butyl-lithium (1.6M solution in hexane 80 mls, 0.1204m) at -100° C. The mixture was then stirred for five minutes before adding trimethyl borate (25 mls, 0.2178 m) at -100° C. The mixture was then allowed to warm to 20° C. before adding it to 100 mls of 10% HCL. The organic layer was then separated and the aqueous layer extracted twice with dichloromethane (100 mls). The organic layers were then combined and washed till acid free with water. The solution was then dried using magnesium sulphate and evaporated to give 4-cyanophenyl boronic acid as an off-white solid 93% yield) which was dried under vacuum.

Provenance & Evidence