Hydrochloric Acid → 1-(3-Fluoro-4-methoxyphenyl)hexan-1-one

Reaktionsgleichung

[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13].[C:14](Cl)(=[O:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].Cl>>[F:5][C:6]1[CH:11]=[C:10]([C:14](=[O:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:9]=[CH:8][C:7]=1[O:12][CH3:13]

Komponenten

Edukt 4

HCID 313Hydrochloric Acid

HCID 67340Hexanoyl chloride

HCID 675762-Fluoroanisole

HCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 219909101-(3-Fluoro-4-methoxyphenyl)hexan-1-oneAusbeute 90,4 %

Versuchsvorschrift

Aluminum chloride (6.5 g, 48.8 mmol) was added to a stirred mixture of 1-fluoro-2-methoxybenzene (5.0 mL, 44.4 mmol) and hexanoyl chloride (7.5 mL, 53.3 mmol) at room temperature. The mixture warmed and HCl evolution occurred. The resulting mixture was stirred at room temperature for 45 minutes and then partitioned between EtOAc (100 mL) and water (100 mL). The EtOAc layer was washed with water (100 mL), aqueous K2CO3 (100 mL) and brine (50 mL), dried over MgSO4, filtered, and evaporated under vacuum to yield crude 1-(3-fluoro-4-methoxyphenyl)-1-hexanone (9 g) as a solid.