Triisopropyl borate → HCID 57423217, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of isobutyl 4-bromobenzenesulfonate (56 g, 200 mmol) in 280 ml of THF was added triisopropylborate (84 ml, 1.82 eq) and the reaction mixture was cooled to less than −65° C. To the cooled solution, n-butyllithium (144 ml, 0.9 eq, 1.07 M in hexanes) was slowly added while maintaining the temperature below −65° C. The reaction mixture was stirred for at least 0.5 hours and then was quenched with 1M sulfuric acid (200 ml). The reaction mixture was allowed to warm to ca. 20° C. The layers were separated and the rich organic layer containing 35 g (92% yield) of 4-(isobutoxysulfonyl)phenylboronic acid was used without further purification in the next step.

Provenance & Evidence