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

HRID 18193

Reaction equation

HRID 18193 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 593449231-[7-Bromo-5-fluoro-3-(3-fluoro-benzyl)-benzofuran-2-yl]-ethanoneYield 82.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-9906a3984f9942d18f576e2eb827c245
Source dataset
uspto-grants-2010_06
Patent number
US07741326B2

Linked notes

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