N-(4-chloro-3-(trifluoromethyl)phenyl)pivalamide synthesis

Yield:13691-92-4 95%

Reaction Conditions:

in triethylamine;

Steps:

18.A 18A.

18A. N-(4-Chloro-3-trifluoromethylphenyl)-2,2-dimethylpropionamide To a solution of commercially available 4-chloro-3-(trifluoromethyl)aniline (15.0 g, 76.7 mmol) in anhydrous THF (200 mL) cooled to 0-5° C. was added triethylamine (11.7 mL, 84.4 mmol) followed by pivaloyl chloride (10.4 mL, 84.4 mmol) over 30 min. The ice bath was removed and the mixture stirred at rt for 1 h. The mixture was diluted with ether and filtered. The filtrate was washed with water (2*) and brine, dried (MgSO₄), filtered and concentrated. The residue was triturated with hexanes and the solid was filtered and dried under vacuum to afford compound 18A (20.4 g, 95%); MS (ES) m/z 280 [M+1]⁺.

References:

US2004/19063,2004,A1 US2004/181064,2004,A1