Water → HCID 58203950、化合物

反応式

[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].CC(=O)CC.O.[Br:24][CH2:25][CH2:26]Br>>[Br:24][CH2:25][CH2:26][O:11][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=1[C:8](=[O:10])[CH3:9]

参加物

反応物 5

HCID 962Water

HCID 6569Methyl Ethyl Ketone

HCID 78391,2-Dibromoethane

HCID 11430Potassium Carbonate

HCID 959922-Acetyl-4-fluorophenol

生成物 1

HCID 58203950HCID 58203950、化合物収率 21.9%

実験手順

Dissolved 1-(5-fluoro-2-hydroxyphenyl)ethanone (10.0 g, 64.9 mmol) in 18 mL 1,2-Dibromoethane and added Potassium carbonate (18.8 g, 136 mmol) and 100 mL 2-Butanone. Heated the reaction mixture to reflux and allowed to stir overnight under nitrogen. Reaction was complete by LCMS. Diluted reaction mixture with water and extracted the product with ethyl acetate. Concentrated in vacuo and purified by flash chromatography (0 to 30% ethyl acetate/heptanes) to give 3.71 g (21.9% yield) of 1-(2-(2-bromoethoxy)-5-fluorophenyl)ethanone.