Toluene → 5-BROMO-2-ETHYLBENZOFURAN

HRID 1699844Notes

Reaction equation

HRID 1699844 reaction equation
[C:1]([C:4]1[O:8][C:7]2[CH:9]=[CH:10][C:11]([Br:13])=[CH:12][C:6]=2[CH:5]=1)(=O)[CH3:2].O.NN.[OH-].[K+].C1(C)C=CC=CC=1>C(O)CO.O>[Br:13][C:11]1[CH:10]=[CH:9][C:7]2[O:8][C:4]([CH2:1][CH3:2])=[CH:5][C:6]=2[CH:12]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 7056701-(5-Bromo-1-benzofuran-2-yl)ethan-1-one

Product 1

HCID 122474825-BROMO-2-ETHYLBENZOFURANYield 88.2%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

2-Acetyl-5-bromobenzo[b]furan (10.00 g) and hydrazine monohydrate (8.00 g) were stirred in ethylene glycol (60 ml) at 150° C. for 2 hr. After cooling, potassium hydroxide (9.00 g) was added and the mixture was stirred at 150° C. for 2 hr. After cooling, toluene (200 ml) and water (100 ml) were added and the separated toluene layer was washed with 10% aqueous solution (100 ml) of ammonium chloride, dried over magnesium sulfate and concentrated to give the objective compound (8.30 g).

Workup

  1. temperatureAfter cooling
  2. temperatureAfter cooling
  3. washthe separated toluene layer was washed with 10% aqueous solution (100 ml) of ammonium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-577b1c1599d14636aa463c8b6f38340f
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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