Dimethylformamide → HCID 53417502, compound

To a solution of 3-bromo-5-(trifluoromethyl)benzoic acid (50 g, 186 mmol) in DCM (500 mL) at 0° C., was added Oxalyl chloride (30.7 g, 242 mmol) with catalytical amount of DMF (0.5 mL). After stirring for 30 min the reaction mixture was concentrated. To a suspension of N,O-dimethylhydroxylamine hydrochloride (23.5 g, 242 mmol) in DCM (300 mL) at 0° C. was added TEA (51 g, 500 mol). Then a solution of acid chloride in DCM (300 mL) was added slowly. After stirring for 1 h, the reaction mixture was poured into water (200 mL) with vigorous stirring, extracted with DCM (2×200 mL). The organic layers were washed with brine (50 mL), dried over anhydrous MgSO4 and then concentrated. The residue was purified by silica gel chromatography (PE/EtOAc=20/1 to 5/1) to give the title compound (47 g, yield: 81%); m/z (ES+): 312 [M+H]+.

1. concentrationwas concentrated
2. stirringAfter stirring for 1 h
3. extractionextracted with DCM (2×200 mL)
4. washThe organic layers were washed with brine (50 mL)
5. dry with materialdried over anhydrous MgSO4
6. concentrationconcentrated
7. customThe residue was purified by silica gel chromatography (PE/EtOAc=20/1 to 5/1)

ORD record

ord-1fb35e4fe9194fd5be937166ec0a3e72

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181259B2