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 EtOAc (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 EtOAc (150 mL). The resulting mixture is then stirred for 30 min at ambient temperature. The mixture is extracted with EtOAc (3×100 mL) and the combined extracts are sequentially washed with hydrochloric acid (2×100 mL of 2M), 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 EtOAc-hexane to give the title compound as a beige crystalline solid, m.p. 157–158° C.

1. extractionThe mixture is extracted with EtOAc (3×100 mL)
2. washthe combined extracts are sequentially washed with hydrochloric acid (2×100 mL of 2M), 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 EtOAc-hexane

ORD record

ord-fc201deeec7d410ea7b4430c763c67dc

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07067543B2