1,1,2,2-Tetrachloroethane → HCID 44203047, compound

To a solution of 3,6-difluorophthalic anhydride (3.0 g, 16.00 mmol) in 1,1,2,2-tetrachloroethane (30 mL) chlorobenzene (2.0 mL, 18.00 mmol) was added followed by the addition of aluminum chloride (4.40 g, 33.00 mmol). The reaction mixture was stirred at room temperature for 120 minutes followed by the stirring at 60° C. for an additional 90 minutes. It was cooled to room temperature, poured into ice water (300 mL) and diluted with 1M aqueous hydrochloric acid. The aqueous slurry was extracted with ethyl acetate (300 mL) and the organic layer was washed with water (70 mL), brine (70 mL) and dried over anhydrous sodium sulfate. Filtration and concentration resulted in a crude product, which was crystallized from ethyl acetate by the addition of hexane. The product was collected by filtration and dried in vacuo to give 2-[(4-chlorophenyl)carbonyl]-3,6-difluorobenzoic acid (3.52 g, 73% yield). 1HMR (400 MHz, CD3OD): 7.77 (s, 1H), 7.75 (s, 1H), 7.53 (s, 1H), 7.51 (s, 1H), 7.53-7.34 (m, 2H). MS (EI) for C14H7ClF2O3: 281 (M−H2O).

1. customstirring at 60° C.
2. customfor an additional 90 minutes
3. temperatureIt was cooled to room temperature
4. extractionThe aqueous slurry was extracted with ethyl acetate (300 mL)
5. washthe organic layer was washed with water (70 mL), brine (70 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationFiltration and concentration
8. customresulted in a crude product, which
9. customwas crystallized from ethyl acetate by the addition of hexane
10. filtrationThe product was collected by filtration
11. customdried in vacuo

ORD record

ord-52532a0b2ef34bbdb3c81450b53f92ca

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697737B2