Ethyl Acetate → 2,3,5-trifluoro-N-(2-fluoro-4-iodophenyl)-6-nitroaniline

Participants

Reaction Conditions

Reaction Steps

1.0M LHMDS in hexane (153 mL, 153 mol) was added drop wise to a solution of 2-fluoro-4-iodoaniline (30.0 g, 128 mol) in dry THF (600 mL) at −78° C. over a period of 30 minutes and the resulting mixture was stirred at −78° C. for 30 minutes. This was followed by the addition of 2,3,4,6-tetrafluoronitrobenzene (25 g, 128 mol) in dry THF (150 mL) and stirring was continued for a further 1 hour at room temperature. The reaction was monitored by TLC (10% ethyl acetate in hexane). The reaction mixture was quenched with 2N HCl (100 mL), concentrated and the concentrate was partitioned between water (500 mL) and ethyl acetate (300 mL). The aqueous layer was washed with ethyl acetate (2×200 mL). The combined organic phase was washed with water, brine solution, dried over anhydrous Na2SO4 and concentrated to afford 38 g of the crude product. Purification by column chromatography on silica gel (0-5% ethyl acetate in hexane) afforded 31 g of the product (58.8% yield). LCMS: 95.5%, m/z=410.9 (M−1).

Provenance & Evidence