Hydrochloric Acid → HCID 68289974, compound

Temperature

-10 °C

To a tetrahydrofuran solution (5.0 mL) of 3-bromo-2-(trifluoromethyl)thiophene (500 μL, 2.08 mmol), lithium diisopropylamide (2.06 mL, 2.29 mmol) was added under nitrogen atmosphere at −40° C., and the resultant mixture was stirred for 30 minutes. To the reaction solution, paraformaldehyde (68.8 mg, 2.29 mmol) was added and the resultant mixture was stirred for 30 minutes, followed by raising the temperature of the mixture to −10° C. The mixture was stirred at −10° C. for 4 hours and at 0° C. for 1 hour. After completion of the reaction, a 1 M hydrochloric acid was added to the reaction solution and extraction from the resultant mixture with ethyl acetate was performed. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (106 mg, yield 20%).

1. customAfter completion of the reaction
2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated under reduced pressure
5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-b23ec9d45ba74c4e93beabbee7aae5cc

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403798B2