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

HRID 268386Notes

Reaction equation

HRID 268386 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 2 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 2 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-5b72da4bd9df435b8e7ce97f9d0098c5
Source dataset
uspto-grants-1976_03
Patent number
US03947470

Reaction notes

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