4-Ethylaniline → N-(2',3',6'-trifluorophenyl)-4-ethylanilin

Participants

Reaction Steps

To a solution of 1.21 g of 4-ethylaniline, 1.10 g of 2,3,6-trifluoro-bromobenzene in 10 g of toluene is added consecutively 350 mg BINAP and 300 mg of bis-dibenzylideneaceton-palladium (0) [Pd(dba)2) in 3 ml of toluene and 0.9 g of sodium tert.-butoxide in 3 ml toluene. The mixture is flushed with nitrogen and heated for 6 h under reflux. After cooling to room temperature, water (30 ml), concentrated hydrochloric acid (10 ml) and hyflo (1 g) are added and stirring is continued for 1 h. The mixture is filtered and the filtrate is separated into its phases. The organic phase is washed three times with water, dried using magnesium sulfate and evaporated to dryness. The residue can be used as such in the following step or purified by flash chromatography on silica using toluene as the eluent affording 1.13 g of N-(2′,3′,6′-trifluorophenyl)-4-ethylanilin.

Provenance & Evidence