tert-Butyl acetate → Ethyl 2-(tert-butoxy)-2-(3,5-dibromothiophen-2-yl)acetate

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-(3,5-dibromothiophen-2-yl)-2-hydroxyacetate (7b) (100 mg, 0.29 mmol) was dissolved in tert-butyl acetate (5.4 mL) at −20° C. and 70% perchloric acid (0.7 mL) was rapidly added. The mixture was stirred at 0° C. for 3 hours then poured in a saturated solution of potassium carbonate. Layers were separated. The aqueous layer was extracted with ethyl acetate (2×20 mL). The organic layers were washed with brine (10 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to provide ethyl 2-(tert-butoxy)-2-(3,5-dibromothiophen-2-yl)acetate (100 mg, 0.40 mmol, 86%).

Provenance & Evidence