3-(Trifluoromethyl)aniline → HCID 1214264, compound

Participants

Reaction Steps

Dissolve 4-bromophenylacetic acid (10.00 g, 46.50 mmol), diisopropylethylamine (12.02 g, 16.20 mL, 93.00 mmol) and 1,1′-carbonyldiimidazole (8.29 g, 51.15 mmol) in tetrahydrofuran (200 mL) at room temperature. Stir the contents under nitrogen for one hour. Add m-trifluoromethylaniline (15.00 g, 93.00 mmol) and stir the reaction overnight at room temperature. Concentrate the reaction to near dryness, dissolve in dichloromethane (250 mL) and extract with 2 N NaOH (200 mL), water (100 mL) and 1 N HCl (2×200 mL). Wash the organic layer with saturated aqueous saturated sodium chloride (100 mL), dry over MgSO4, filter and concentrate. Dry load the material onto silica (100 g) and chromatograph on silica using dichloromethane as eluent to yield the product (13.00 g, 78.1%). MS(ES), m/z 356/358 (M+1).

Provenance & Evidence