Bromomethyl 4-methoxyphenyl ketone → 5-Bromo-2-(4-methoxybenzoyl)benzofuran

HRID 1901330

Reaction equation

HRID 1901330 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH2:21]Br)=[O:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:21]([C:19](=[O:20])[C:16]3[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=3)=[CH:7][C:6]=2[CH:9]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 11430Potassium CarbonateHCID 728635-Bromosalicylaldehyde

Product 1

HCID 23717245-Bromo-2-(4-methoxybenzoyl)benzofuranYield 42.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 150 ml of acetone were suspended 20 g of 5-bromosalicylaldehyde, 22.9 g of 2-bromo-4-methoxyacetophenone and 27.6 g of anhydrous potassium carbonate. After stirring at room temperature for 4 hours, the resulting reaction solution was concentrated to dryness, and then mixed with water to collect precipitated crystals by filtration. After washing with water and subsequent recrystallization from ethanol, 14.02 g of 5-bromo-2-(4-methoxybenzoyl)benzofuran was obtained in the form of colorless prism crystals.

Workup

  1. customthe resulting reaction solution
  2. concentrationwas concentrated to dryness
  3. additionmixed with water
  4. customto collect
  5. customprecipitated crystals
  6. filtrationby filtration
  7. washAfter washing with water and subsequent recrystallization from ethanol

Sources & evidence

ORD record
ord-fd4f2b0f19b84a09aab15dcf1f9b02ac
Source dataset
uspto-grants-1996_11
Patent number
US05576343

Linked notes

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