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

HRID 361899

Reaction equation

HRID 361899 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-147fa8572d0043199d3c528646185b65
Source dataset
uspto-grants-1999_02
Patent number
US05866577

Linked notes

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