3-Chloro-4-fluoroaniline → 4-Fluoro-3-(thiophen-2-yl)aniline

Participants

Reaction Conditions

Reaction Steps

768 mg of thiophene-2-boronic acid, 90 mg of palladium(II) acetate, 328 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl, 1.7 g of potassium phosphate and 562 mg of 3-chloro-4-fluoroaniline were added to 8 ml of dry toluene. The mixture was stirred at 80° C. overnight under an argon atmosphere. The cooled reaction mixture was admixed with water and ethyl acetate, and filtered, and the filtrate was extracted by shaking three times with a mixture of ethyl acetate and toluene. The combined organic phases were dried over magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The chromatographic purification of the residue was effected by method [RP1]. 4-Fluoro-3-thiophen-2-yl-phenylamine (267.4) was obtained. Molecular weight 193.03 (C10H8FNS); retention time Rt=1.18 min. [B]; MS (ESI): 235.08 (MH++CH3CN).

Provenance & Evidence