Cesium carbonate → 5-Fluoro-2-(2,2,2-trifluoroethoxy)nitrobenzene

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 3.14 g of 4-fluoro-2-nitrophenol, 13 g of cesium carbonate and 20 mL of anhydrous dimethylformamide was heated at 100° C. for 4 hours. After this period, 6.65 g of 2,2,2-trifluoroethyl p-toluenesulphonate was added and the mixture was stirred at the same temperature for 40 hours. Afterwards, the solvent was removed under reduced pressure at 35° C. and 50 mL of water was added to the residue. The mixture was acidified with 37% hydrochloric acid and extracted with 3×40 mL of ethyl acetate. The organic layer was washed with 20 mL of brine, dried over sodium sulphate and evaporated to dryness in vacuo. The residue was purified by flash chromatography (petroleum ether:ethyl acetate 100:7) to afford 1.53 g (32%) of Compound 5A as an oil.

Provenance & Evidence