Pivaloyl chloride → HCID 68871083, compound

Participants

Reaction Steps

To a solution of 1-{[(2-amino-4-bromophenyl)amino]ethyl}cyclohexanol (Step B, 892 mg, 2.8 mmol) in toluene (15 mL) was added pivaloyl chloride (379 μL, 3.1 mmol) at room temperature. After stirring for 15 min, p-toluenesulfonic acid monohydrate (533 mg, 2.8 mmol) was added and the mixture was stirred under reflux for 17 h with Dean-Stark apparatus. Water (5 mL) and saturated sodium hydrogencarbonate aqueous solution were added and the mixture was extracted with ethyl acetate (15 mL×3). The organic extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1 then 4:1 as eluent) to afford the title compound (215 mg, 21%).

Provenance & Evidence