Potassium Hydroxide → 5-Bromo-2-(4-methoxybenzyl)benzofuran

HRID 1738704Notes

Reaction equation

HRID 1738704 reaction equation
[OH-].[K+].O.O.NN.[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([C:16](=O)[C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[CH:13][C:12]=2[CH:26]=1>C(O)COCCO>[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)=[CH:13][C:12]=2[CH:26]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 23717245-Bromo-2-(4-methoxybenzoyl)benzofuranHCID 22141362Hydrazine--water (1/2)

Product 1

HCID 218443705-Bromo-2-(4-methoxybenzyl)benzofuranYield 82.5%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

5.07 g of potassium hydroxide was added to 30 ml of diethylene glycol, and the mixture was stirred at room temperature during which 5.5 g of 80% hydrazine dihydrate.2H2O and 5.0 g of 5-bromo-2-(4-methoxybenzoyl)-benzofuran were further added. The thus prepared mixture was refluxed under heating. After cooling, the resulting reaction solution was adjusted to pH 4-5, extracted with benzene, and then dried. After distilling off the solvent, the resulting residue was purified by subjecting it to silica gel column chromatography using a n-hexane/isopropanol mixture as an elution solvent, thereby obtaining 3.95 g of 5-bromo-2-(4-methoxybenzyl)benzofuran as a brown oily material.

Workup

  1. temperatureThe thus prepared mixture was refluxed
  2. temperatureunder heating
  3. temperatureAfter cooling
  4. customthe resulting reaction solution
  5. extractionextracted with benzene
  6. customdried
  7. distillationAfter distilling off the solvent
  8. customthe resulting residue was purified

Sources & evidence

ORD record
ord-eed1ef42a22940278fa467e9ff0405c0
Source dataset
uspto-grants-1999_10
Patent number
US05962695

Reaction notes

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