3-(Trifluoromethyl)aniline → HCID 24762957, compound

Participants

Reaction Conditions

Reaction Steps

In a dried vessel, 55 μl (0.44 mMol) 3-trifluoromethyl-aniline are dissolved in 6 ml toluene and cooled in an ice bath. Then 0.66 ml Me3Al (2 M in toluene; 1.32 mMol) are added via syringe. After 1 h at rt, a solution of 156 mg (0.40 mMol) 6-(6-benzyloxymethyl-pyrimidin-4-yloxy)-benzofuran-3-carboxylic acid methyl ester in 2 ml THF is added and the yellowish solution is stirred for 1¼ h in an oil bath of 110° C. The solution is cooled in an icebath and hydrolyzed with 15 ml of a sat. NH4Cl solution. After 15 min stirring, the mixture is diluted with EtOAc and water, the aq. phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; hexane/EtOAc 4:1→EtOAc) gives the title compound: MS: [M+1]+=520; TLC(hexane/EtOAc 2:1): Rf=0.17.

Provenance & Evidence