2-Nitrobenzoyl chloride → N-[4-bromo-3-(trifluoromethyl)phenyl]-2-nitrobenzamide

A solution of 3-amino-6-bromobenzotrifluoride (Fluka, Buchs, Switzerland; 24.0 g, 100 mmol) in ethyl acetate (240 mL) is added to a stirred aqueous solution of sodium hydroxide (110 mL of 1 M) at room temperature. This stirred solution is then treated dropwise over 30 minutes with a solution of 2-nitrobenzoyl chloride (Fluka, Buchs, Switzerland; 14.5 mL, 110 mmol) in ethyl acetate (150 mL). The resulting mixture is then stirred for 30 min at ambient temperature. The mixture is extracted with ethyl acetate (3×100 mL) and the combined extracts are sequentially washed with hydrochloric acid (2×100 mL of 2 M), water (2×100 mL), saturated aqueous sodium hydrogen carbonate solution (2×100 mL) and saturated aqueous sodium chloride (1×100 mL), dried (MgSO4), filtered and the solvent is evaporated under reduced pressure to yield the crude product which is purified by recrystallisation from ethyl acetate-hexane to give the title compound as a beige crystalline solid, m.p. 157-158° C.

1. extractionThe mixture is extracted with ethyl acetate (3×100 mL)
2. washthe combined extracts are sequentially washed with hydrochloric acid (2×100 mL of 2 M), water (2×100 mL), saturated aqueous sodium hydrogen carbonate solution (2×100 mL) and saturated aqueous sodium chloride (1×100 mL)
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. customthe solvent is evaporated under reduced pressure
6. customto yield the crude product which
7. customis purified by recrystallisation from ethyl acetate-hexane

ORD record

ord-212a2eed43d0428d8abae148223df8ff

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07482369B2