Water → Tert-butyl 4-(2-(dimethylamino)ethoxy)-2-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-dimethylaminoethanol (6.67 mL, 64.8 mmol) in anhydrous tetrahydrofuran (100 mL), at 0° C., potassium tert-butoxide (6.66 g, 59.4 mmol) was added. The mixture was stirred at 0° C. for 1 h, then 4-fluoro-2-nitro-benzoic acid tert-butyl ester (10 g, 41.5 mmol) in anhydrous tetrahydrofuran (50 mL) was added dropwise. After 2 hours at 0° C., the mixture was poured into water (1 L) and extracted with ethyl acetate (4×200 mL). The organic phase was washed with water, brine, dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The crude was purified by flash chromatography, using dichloromethane-methanol-33% NH4OH 9:1:0.01 as eluant, to give the title compound (4.53 g) as yellow oil.

Provenance & Evidence