4-Chloroaniline → 4-Bromo-N-(2,2-dichloro-1-(4-chlorophenylamino)butyl)benzamide

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Reaction Steps

A solution of 4-bromo-N-(2,2-dichloro-1-hydroxybutyl)benzamide 119 (0.84 g, 2.48 mmol) in chloroform (15 mL) was reacted with PCl5 (0.54 g, 2.46 mmol) at 50° C. for 30 minutes. The mixture was cooled to room temperature and quenched with ice. The aqueous layer was extracted with ether. The organic solution was dried over MgSO4, filtered, and reacted with 4-chloroaniline (0.66 g, 5.17 mmol). The mixture was stirred for 18 hours at room temperature. An acidic, (HCl) aqueous workup and ether extraction preceded chromatographic purification on silica gel (7:3 hexane:CH2Cl2). 4-Bromo-N-(2,2-dichloro-1-(4-chlorophenylamino)butyl)benzamide (Compound-15) was obtained as a white solid (701 mg, 62%). 1H NMR (300 MHz, CDCl3): δ=7.64-7.56 (m, 4H), 7.16 (d, J=9.0 Hz, 2H), 6.73 (d, J=8.7 Hz, 2H), 6.48 (d, J=9.6 Hz, 1H), 6.01 (d, J=9.0 Hz, 1H), 2.50-2.27 (m, 2H), 1.27 (t, J=7.2 Hz, 3H).

Provenance & Evidence