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

HRID 361925Notes

Reaction equation

HRID 361925 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/iso-propanol 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-9ab2948c7f1c4456b15c0b4c457b12f3
Source dataset
uspto-grants-1999_02
Patent number
US05866577

Reaction notes

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