N,N-Dimethylaniline → 2-bromo-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamide

N,N-Dimethylaniline (20.46 g, 168.8 mmol) was added to a solution of 3-amino-2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridine (42.29 g, 139.0 mmol) in dichloromethane (600 mL). While the mixture was stirred under cooling with ice, a solution of bromoacetyl bromide (28.73 g, 142.3 mmol) in dichloromethane (100 mL) was added thereto, followed by stirring for ten minutes. The reaction mixture was diluted with water and then extracted with chloroform. The organic layer was washed with saturated brine and then dried over sodium sulfate anhydrate, followed by concentration under reduced pressure. The thus-obtained crystals were recrystallized from chloroform-hexane, to thereby yield 2-bromo-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamide (50.25 g, yield 85%) as colorless needles.

1. temperatureunder cooling with ice
2. stirringby stirring for ten minutes
3. extractionextracted with chloroform
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over sodium sulfate anhydrate
6. concentrationfollowed by concentration under reduced pressure
7. customThe thus-obtained crystals were recrystallized from chloroform-hexane

ORD record

ord-f52ff6db4e1e4bddbb770aab5a651433

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07223764B2