Acetic Acid → 3-Bromo-7-fluoro-1-benzofuran

HRID 2253688Notes

Reaction equation

HRID 2253688 reaction equation
[OH-].[K+].Br[CH:4]1[O:8][C:7]2[C:9]([F:13])=[CH:10][CH:11]=[CH:12][C:6]=2[CH:5]1[Br:14].C(O)(=O)C>C(O)C>[Br:14][C:5]1[C:6]2[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:7]=2[O:8][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 15158727HCID 15158727, compound

Product 1

HCID 151587283-Bromo-7-fluoro-1-benzofuranYield 97.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of potassium hydroxide (12.7 g) in ethanol (180 ml) was slowly added the product obtained in Step 1 (34 g) and stirred for 3 hours. The resulting solution was neutralized by acetic acid, then extracted with ether. The organic layer was washed with successive water and saturated aqueous NaCl solution. After drying over anhydrous sodium sulfate, ether was removed in vacuo to give 24.1 g of the objective compound.

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with successive water and saturated aqueous NaCl solution
  3. dry with materialAfter drying over anhydrous sodium sulfate, ether
  4. customwas removed in vacuo

Sources & evidence

ORD record
ord-a5866ecb6dbd4ee090e6c5488875246d
Source dataset
uspto-grants-1993_08
Patent number
US05232936

Reaction notes

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