tert-Butyl chloroacetate → t-Butyl 3,5-difluoro4-nitrophenylacetate

Participants

Reaction Conditions

Reaction Steps

A mixture of potassium tert-butoxide (12.3 g, 111.0 mmol) in NMP (100 ml) was cooled to −20° C. under N2. A mixture of 2,6-difluoronitrobenzene (5.0 g, 31.43 mmol) and tert-butylchloroacetate (7.6 ml, 53.11 mmol) in NMP (100 ml) was added slowly at −10° C. to -20° C. over 1.5 hours. After 1.5 hours the reaction was quenched by pouring into 2M HCl (120 ml) and ice, then heptane (300 ml) was added. The mixture was stirred for 10 minutes, separated and the aqueous extracted with heptane (2×400 ml). The organic layer was washed with brine (×2), dried (MgSO4), filtered and washed with heptane. The solution was concentrated in vacuo and the residue purified by column chromatography (3-4% EtOAc/Heptane) to provide the title compound as an orange oil (4.34 g, 53% yield).

Provenance & Evidence