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

HRID 1683687Notes

Reaction equation

HRID 1683687 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-b440da6bf18c4451bca4470adaae49ee
Source dataset
uspto-grants-1997_06
Patent number
US05639753

Reaction notes

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