Dimethylformamide → 5,6-Difluoro-1-indanone

Oxalyl chloride (1.12 mL) and DMF (78.2 mg) were added to a solution of 3,4-difluorohydrocinnamic acid (2.00 g) in dichloromethane (3.0 mL) at 0° C., and the reaction solution was stirred at room temperature overnight. After confirming that the raw materials disappeared, the reaction solution was concentrated under reduced pressure. Next, a solution of the resulting residue in dichloromethane (10 mL) was added to a solution of aluminum chloride (2.13 g) in dichloromethane (20 mL) at −30° C. The reaction solution was stirred at room temperature for 1.5 hours. After confirming that the raw materials disappeared, the reaction solution was poured into ice water. The solution was extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (elution solvent: heptane-ethyl acetate system) to obtain 535 mg of the title compound. The physical properties of the compound are as follows.

1. concentrationthe reaction solution was concentrated under reduced pressure
2. additionNext, a solution of the resulting residue in dichloromethane (10 mL) was added to a solution of aluminum chloride (2.13 g) in dichloromethane (20 mL) at −30° C
3. stirringThe reaction solution was stirred at room temperature for 1.5 hours
4. additionthe reaction solution was poured into ice water
5. extractionThe solution was extracted with ethyl acetate
6. washThe organic layer was washed with brine
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe resulting residue was purified by silica gel chromatography (elution solvent: heptane-ethyl acetate system)

ORD record

ord-80893655517a440bade9c2f99025aad6

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07880009B2