Dichloromethane → 1-[7-Bromo-5-fluoro-3-(3-fluoro-benzyl)-benzofuran-2-yl]-ethanone

HRID 18193

Reaktionsgleichung

Reaktionsgleichung von HRID 18193
[Br:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)[C:6]=2[CH:5]=[C:4]([F:19])[CH:3]=1.[C:20](Cl)(=[O:22])[CH3:21].ClCCl.[Cl-].[Al+3].[Cl-].[Cl-]>Cl>[Br:1][C:2]1[C:10]2[O:9][C:8]([C:20](=[O:22])[CH3:21])=[C:7]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)[C:6]=2[CH:5]=[C:4]([F:19])[CH:3]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 593449097-Bromo-5-fluoro-3-(3-fluoro-benzyl)-benzofuran

Produkt 1

HCID 593449231-[7-Bromo-5-fluoro-3-(3-fluoro-benzyl)-benzofuran-2-yl]-ethanoneAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

7-Bromo-5-fluoro-3-(3-fluoro-benzyl)-benzofuran (1.29 gm, 4 mmol), acetyl chloride (0.57 ml, 8 mmol) and dichloromethane (16 ml) were added to an oven dried flask and chilled in ice bath. Aluminum chloride (1.067 gm, 8 mmol) was added and after 5 minutes the reddish brown mixture was allowed to warm to room temperature and stir overnight. The mixture was diluted with hydrochloric acid (0.1M) and extracted three times with dichloromethane. The extracts were dried over magnesium sulfate and purified by column chromatography (ethyl acetate/hexane gradient) to give 1-[7-Bromo-5-fluoro-3-(3-fluoro-benzyl)-benzofuran-2-yl]-ethanone (1.2 gm, 82% yield).

Aufarbeitung

  1. customdried flask
  2. temperaturechilled in ice bath
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe extracts were dried over magnesium sulfate
  5. custompurified by column chromatography (ethyl acetate/hexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-9906a3984f9942d18f576e2eb827c245
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741326B2

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