Chloroacetyl chloride → 2'-Bromo-5'-trifluoromethyl-2-chloroacetanilide

Temperature

0 °C

To a solution of 2-bromo-5-trifluoromethylaniline (10.0 g) in methylene chloride (100 ml) was added triethylamine and the solution was cooled to 0° C. To this solution was slowly added choroacetyl chloride and the reaction mixture was allowed to cool to room temperature overnight. The solution was concentrated and the resulting solid was extracted with ethyl acetate. The organic extract was first washed with 10% HCl (2×2 ml), then with water (12×25 ml) and was collected, dried and evaporated to obtain the title compound (yield, 10.2 g). 1HNMR (250 MHz, CDCl3): 4.22 (s, 2 H), 7.26 (d, J=8 Hz, 1 H), 7.66 (d, J=8 Hz, 1 Hz), 8.68 (s, 1 H), 9.02 (br s, 1 H).

1. temperatureto cool to room temperature overnight
2. concentrationThe solution was concentrated
3. extractionthe resulting solid was extracted with ethyl acetate
4. extractionThe organic extract
5. washwas first washed with 10% HCl (2×2 ml)
6. customwith water (12×25 ml) and was collected
7. customdried
8. customevaporated

ORD record

ord-c8665eba631f41fd986e3dd0e0027af3

Source dataset

uspto-grants-1994_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05304557