Dimethyl Sulfoxide → HCID 66605156, compound

Participants

Reaction Steps

A flask was charged with 5-bromo-2-fluorobenzonitrile (5 g, 25.00 mmol), ethyl 4-aminobenzoate (4.54 g, 27.5 mmol), and KOtBu (5.11 g, 45.5 mmol). To this was added DMSO (100 mL). After stirring at room temperature for 20 min, the reaction mixture was diluted with ethyl acetate and water. The aqueous was extracted with ethyl acetate, the combined organic was washed with water (3×), brine, dried over MgSO4 and filtered. The filtrate was concentrated. The residue was suspended in ethyl acetate, collected the solid by filtration. Repeated above procedure for several times (each collected solid was checked by LCMS) until the collected solid is pure. The mixture residue was further purified via silica gel chromatography (0-30% ethyl acetate in hexanes) to give total 7.15 g of ethyl 4-(4-bromo-2-cyanophenylamino)benzoate. MS (ESI) m/z 345.2 (M+H). 1H NMR (CDCl3) δ ppm 8.02 (2H, d, J=8.55 Hz), 7.65 (1H, d, J=2.44 Hz), 7.53 (1H, dd, J=9.00, 2.29 Hz), 7.25 (1H, d, J=9 Hz), 7.14 (2H, d, Hz), 6.47 (1H, s), 4.36 (2H, q, J=7.22 Hz), 1.38 (3H, t, J=7.17 Hz).

Provenance & Evidence