Water → 6-Bromo-1-benzofuran

HRID 1690203Notes

Reaction equation

HRID 1690203 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH:10](OCC)OCC)[CH:3]=1.O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[CH:10]=[CH:9][O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 154537651-Bromo-3-(2,2-diethoxyethoxy)benzene

Product 1

HCID 151587226-Bromo-1-benzofuranYield 72.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-bromo-3-(2,2-diethoxyethoxy)benzene (2.3 g, 8.35 mmol) in toluene (28 mL), PPA (5.0 mL) was added, and the resultant mixture was stirred overnight while heated to reflux. The reaction solution was added with water at room temperature and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified using silica-gel column chromatography (hexane). 6-Bromobenzofuran (1.2 g, yield 68%, mixture with 7-bromobenzofuran) was obtained as a yellow oil.

Workup

  1. temperaturewhile heated to reflux
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified

Sources & evidence

ORD record
ord-594f84ec6e024851bd4e1138f6a679b0
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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