Dimethylformamide → HCID 22227324, compound

Temperature

-78 °C

Compound 32 intermediates: To a solution of 4-(trifluorovinyloxy)-bromobenzene (9.25 g, 36.6 mmol) in dry diethyl ether (60 mL) at −78° C. was added t-BuLi (23.7 mL, 1.7 M in pentane) dropwise. One hour later, DMF (4.3 mL, 1.5 eq) was added dropwise. The reaction mixture was stirred at −78° C. for 1 h. Then the reaction mixture was allowed to warm up to room temperature for about 45 min, and quenched by adding water (10 mL). The ethereal layer was collected and the aqueous layer was extracted with diethyl ether. The combined organic layer was washed with water twice (50 mL×2), and dried over sodium sulfate. After filtration and evaporation of the solvent, the product was dried in vacuum overnight to give 4-(trifluorovinyloxy)benzaldehyde as yellow oil, which can be used in next step without further purification. 1H NMR (CDCl3): δ 10.18 (s, 1H), 7.85 (d, J=8.8 Hz, 2H), 7.17 (d, J=8.8 Hz, 2H).

1. temperatureto warm up to room temperature for about 45 min
2. customquenched
3. additionby adding water (10 mL)
4. customThe ethereal layer was collected
5. extractionthe aqueous layer was extracted with diethyl ether
6. washThe combined organic layer was washed with water twice (50 mL×2)
7. dry with materialdried over sodium sulfate
8. filtrationAfter filtration and evaporation of the solvent
9. customthe product was dried in vacuum overnight

ORD record

ord-b8041665613b402fbb247493797aa88f

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07019453B2