Acetic Acid → HCID 57423216, compound

Participants

Reaction Conditions

Reaction Steps

4-bromobenzenesulfonyl chloride 850 g, 0.19 mol) was suspended in 2-propanol (45 ml, 3 eq) and the slurry was cooled to less then 10° C. Pyridine (32 ml, 2 eq) was added in portions while maintaining the reaction temperature below 10° C. After reaction completion (ca. 3 hours), 11 ml of glacial acetic acid followed by 250 ml of methyl tert-butyl ether (MTBE) were added. The layers were separated and the rich organic layer was successively washed with 125 ml of 1N aqueous hydrochloric acid and 150 ml of saturated sodium bicarbonate solutions. The rich MTBE solution was solvent exchanged into hexane (i.e., the addition of hexane with concurrent distillation of MTBE) to induce crystallisation. The crystal slurry was filtered, washed and dried in vacuo at no more than 25° C., to give 48 g (87% yield) of isobutyl 4-bromobenzenesulfonate.

Provenance & Evidence