Potassium Hydroxide → 3-Bromo-1-benzofuran

HRID 1604236Notes

Reaction equation

HRID 1604236 reaction equation
[OH-].[K+].Br[CH:4]1[CH:8]([Br:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[O:5]1>C(O)C>[Br:9][C:8]1[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[O:5][CH:4]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 123940372,3-Dibromo-2,3-dihydrobenzofuran

Product 1

HCID 6405893-Bromo-1-benzofuranYield 108%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To 11.3 g KOH (176 mmol) in 100 mL ethanol at 0° C. was added in small portions 22.2 g of 2,3-dibromo-2,3-dihydrobenzofuran, and the resulting reaction mixture was stirred at 0° C. for an additional 3 h. Most of the solvent was then removed in vacuo. Water and ether were added to the residue. The aq layer was separated and extracted with ether. The combined ether layers were washed with water and brine, dried (MgSO4), and concentrated to give 17 g of 3-bromobenzofuran.

Workup

  1. customthe resulting reaction mixture
  2. customMost of the solvent was then removed in vacuo
  3. additionWater and ether were added to the residue
  4. customThe aq layer was separated
  5. extractionextracted with ether
  6. washThe combined ether layers were washed with water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2265f6c0f21e4725bfa14457e4adc82c
Source dataset
uspto-grants-1999_11
Patent number
US05994270

Reaction notes

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