Water → 6-Bromo-1-benzofuran

HRID 1038580Notes

Reaction equation

HRID 1038580 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), was added PPA (5.0 mL) and refluxed for overnight. The reaction solution was added 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 by silica-gel column chromatography (hexane). The title compound (1.2 g (yield 68%, mixture with 7-bromobenzofuran)) was obtained as a yellow oil.

Workup

  1. temperaturerefluxed for overnight
  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 by silica-gel column chromatography (hexane)

Sources & evidence

ORD record
ord-23f29aeb25d443e289ced8877ec25bbe
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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