t-Butyl bromide → Tert-butyl 2-(4-fluoroanilino)-4-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

To N,N-dimethylacetamide 15 mL solution of 2-(4-fluoroanilino)-4-nitrobenzoic acid 1.0 g, were added potassium carbonate 9.9 g, benzyltriethylammonium chloride 0.82 g and 2-bromo-2-methylpropane 21 mL at room temperature, and it was stirred at 55° C. for 4 hours. After the reaction mixture was cooled to room temperature,2-bromo-2-methylpropane 21 mL was added to it, and it was stirred at 55° C. for 12 hours. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with water and 10% citric acid aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate=8:1] to give tert-butyl 2-(4-fluoroanilino)-4-nitrobenzoate 1.1 g of red oil.

Provenance & Evidence