2,3,5,6-tetrafluoro-4-phenylaniline

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N-dimethyl-2-iodophenylacetamide (2.0 g, 6.9 mmol), 2,3,5,6-tetrafluoro-4-phenylaniline (3.3 g, 13.8 mmol), copper powder (219 mg, 3.4 mmol), copper(I) iodide (646 mg, 3.4 mmol) and anhydrous potassium carbonate (1.0 g, 6.9 mmol) are stirred together in 150 mL of xylenes. The reaction is heated to reflux temperature for 48 hours. While still slightly warm (40° C.) the brown suspension is filtered through a pad of Celite which in turn is rinsed with toluene (250 mL). The filtrate is evaporated by rotary evaporator and then flash chromatographed on silica gel (10–20% EtOAc/hexane) to give the title product. The reaction is heated to reflux temperature for 48 hours is filtered through a pad of Celite which in turn is rinsed with toluene (250 mL) The filtrate is evaporated by rotary evaporator flash chromatographed on silica gel (10–20% EtOAc/hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,3,5,6-Tetrafluoro-4-bromoaniline (13.8 g, 56.7 mmol) is dissolved in benzene (200 mL) and treated with 1.5 equivalents of phenylboronic acid (10.4 g, 85.1 mmol) and a catalytic amount of tetrakistriphenylphosphine palladium(0) (4.2 g, 3.6 mmol) as a solution in ethanol (30 mL). Sodium carbonate (60 mL of 2 M aqueous solution) is added and the reaction mixture stirred and heated to reflux temperature for 24 hours. After cooling to room temperature the mixture is partitioned between Et2O (500 mL) and water (250 mL). The organic layer is washed with brine, dried (MgSO4) and concentrated by rotary evaporator. The residual oil is purified by flash chromatography (9:1 hexanes/EtOAc) to give 2,3,5,6-tetrafluoro-4-phenylaniline as an oil. heated to reflux temperature for 24 hours is partitioned between Et2O (500 mL) and water (250 mL) The organic layer is washed with brine dried (MgSO4) concentrated by rotary evaporator The residual oil is purified by flash chromatography (9:1 hexanes/EtOAc)