1,3,5-Trifluoro-2-nitrobenzene → HCID 57625029, compound

Participants

Reaction Steps

25 g 1,3,5-trifluoro-2-nitrobenzene (141.2 mmol, 1 eq.) and 33.5 g 2-fluoro-4-iodoaniline (141.2 mmol. 1 eq.) were dissolved in 250 mL dry THF and cooled with ice-salt to −10 to 0° C. upon which 424 mL lithium hexamethyldisilazide (LiHMDS) solution (1M in THF; 424 mmol, 3. eq.) were added slowly over a 1 h periode. Upon completion of addition of base, the reaction mixtures was allowed to warm to rt and stirring was continued for 5 days. The reaction mixture was quenched with 0.5 N hydrochloric acid and diluted with ethyl acetate. Saturated ammonium chloride solution was added to facilitate phase separation. The separated aqueous phase was reextracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give dark solid residue. The residue was purified by flash column chromatography on silica gel with hexane and hexane/ethyl acetate 8:2 as eluent to yield 45.8 gram (82% yield) of the analytically pure target compound as a slightly brownish solid.

Provenance & Evidence