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

HRID 1738679Notes

Reaction equation

HRID 1738679 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-651a8323cf72433bb8932680c98f9817
Source dataset
uspto-grants-1999_10
Patent number
US05962695

Reaction notes

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