Diethylene Glycol → 2-Benzyl-5-bromo-1-benzofuran

HRID 1577028Notes

Reaction equation

HRID 1577028 reaction equation
[C:1]([C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:12]=2[CH:13]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN.C(O)COCCO.[OH-].[K+]>O>[CH2:1]([C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:12]=2[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 801609(5-bromo-1-benzofuran-2-yl)(phenyl)methanone

Product 1

HCID 227689092-Benzyl-5-bromo-1-benzofuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 42.2 g. (0.14 mol.) of 2-benzoyl-5-bromobenzofuran and 35 ml. of 98% hydrazine in 70 ml. of diethylene glycol is warmed for a few minutes on a steam bath. Then 23.3 g. of potassium hydroxide is added and the reaction mixture is refluxed for two hours. After cooling, water is added to the mixture and the resulting aqueous solution is extracted with benzene. The extract is washed with water, 10% aqueous hydrochloric acid and water, dried (MgSO4) and concentrated to yield 2-benzyl-5-bromobenzofuran.

Workup

  1. additionA mixture of 42.2 g
  2. temperaturethe reaction mixture is refluxed for two hours
  3. temperatureAfter cooling
  4. extractionthe resulting aqueous solution is extracted with benzene
  5. washThe extract is washed with water, 10% aqueous hydrochloric acid and water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b1a2b30d61324995bbaef2cd1006242f
Source dataset
uspto-grants-1976_09
Patent number
US03983245

Reaction notes

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