Potassium Acetate → 3-Acetoxy-7-bromo-2,3-dihydro-2,2-dimethylbenzofuran

HRID 440910Notes

Reaction equation

HRID 440910 reaction equation
Br[CH:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([Br:11])[C:5]=2[O:4][C:3]1([CH3:13])[CH3:12].[C:14]([O-:17])(=[O:16])[CH3:15].[K+]>CN(C)C=O>[C:14]([O:17][CH:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([Br:11])[C:5]=2[O:4][C:3]1([CH3:13])[CH3:12])(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 190407783,7-Dibromo-2,3-dihydro-2,2-dimethylbenzofuran

Product 1

HCID 190407903-Acetoxy-7-bromo-2,3-dihydro-2,2-dimethylbenzofuran

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7.6 grams (0.025 mole) of 3,7-dibromo-2,3-dihydro-2,2-dimethylbenzofuran and 11.3 grams (0.115 mole) of powdered potassium acetate in 125 mL of dry N,N-dimethylformamide is stirred at ambient temperature for about 24 hours. After this time, the reaction mixture is concentrated under reduced pressure to a residue. The residue is poured into about 350 mL of water and the mixture is extracted with diethyl ether. The ether extract is concentrated under reduced pressure, yielding 3-acetoxy-7-bromo-2,3-dihydro-2,2-dimethylbenzofuran.

Workup

  1. concentrationAfter this time, the reaction mixture is concentrated under reduced pressure to a residue
  2. additionThe residue is poured into about 350 mL of water
  3. extractionthe mixture is extracted with diethyl ether
  4. extractionThe ether extract
  5. concentrationis concentrated under reduced pressure

Sources & evidence

ORD record
ord-f2d5c4cb2f5045a98fd505a5191bdcf7
Source dataset
uspto-grants-1996_05
Patent number
US05521190

Reaction notes

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