2-Fluorobenzoyl chloride → HCID 15728739, compound

Temperature

0 °C

To 3-thiophenecarboxaldehyde dimethylacetal (50.6 g) and ether (500 ml) was added n-butyllithium (132 ml, 2.5M in hexanes) at a rate so as to maintain gentle reflux of the mixture. The reaction mixture was heated at reflux an additional 30 mins, diluted with tetrahydrofuran (600 ml), and cooled to 0° C. A solution of 2-fluorobenzoyl chloride (44.0 ml, 368 mmol) and tetrahydrofuran (500 ml), precooled to -78° C., was added with stirring. The mixture was stirred at -78° C. for 1 hr and then allowed to warm to room temperature overnight. Dilute aqueous ammonium chloride solution and ether were added and the layers were separated. The organic layer was washed with dilute aqueous sodium bicarbonate solution, and the combined aqueous layers were back-extracted with ether. The combined organic layers were washed with brine, dried over anhydrous potassium carbonate, filtered, and concentrated to give 2-(2-fluorobenzoyl)-3-thiophenecarboxaldehyde dimethylacetal.

1. temperatureto maintain gentle
2. temperaturereflux of the mixture
3. temperatureThe reaction mixture was heated
4. temperatureat reflux an additional 30 mins
5. customprecooled to -78° C.
6. additionwas added
7. stirringThe mixture was stirred at -78° C. for 1 hr
8. temperatureto warm to room temperature overnight
9. customthe layers were separated
10. washThe organic layer was washed with dilute aqueous sodium bicarbonate solution
11. extractionthe combined aqueous layers were back-extracted with ether
12. washThe combined organic layers were washed with brine
13. dry with materialdried over anhydrous potassium carbonate
14. filtrationfiltered
15. concentrationconcentrated

ORD record

ord-496de884f1d34c69b3886edff1510378

Source dataset

uspto-grants-1993_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05227388