Hexamethylphosphoramide → 1-Fluoro-4-(pent-4-YN-1-YL)benzene

Subsequently, sodium acetylide (18% slurry in xylene) (50 ml) was added to hexamethylphosphoramide (20 ml) with stirring, and to the resulting mixture was furthermore added a solution of 3-(4-fluorophenyl)-1-iodopropane (7.00 g, 26.5 mmol) obtained above in dry dimethylformamide (20 ml) with stirring under ice-cooling, and then the resulting mixture was stirred at room temperature for 2 hours. After stirring, ice-cold water was added to the reaction mixture carefully with stirring under ice-cooling, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by flash chromatography on a silica gel column using hexane as the eluent to afford the title compound (2.67 g, yield: 62%) as a colorless oil.

1. stirringwith stirring under ice-
2. temperaturecooling
3. stirringthe resulting mixture was stirred at room temperature for 2 hours
4. stirringAfter stirring
5. additionice-cold water was added to the reaction mixture carefully
6. stirringwith stirring under ice-
7. temperaturecooling
8. extractionthe resulting mixture was extracted with ethyl acetate
9. washThe organic layer was washed with saturated aqueous sodium chloride solution
10. dry with materialdried over anhydrous magnesium sulfate
11. filtrationAfter filtration
12. customthe solvent was removed in vacuo
13. customthe residue was purified by flash chromatography on a silica gel column

ORD-Eintrag

ord-32ac9f7b29da47319af72aa705a8a5d5

Quelldatensatz

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08101650B2