Ethyl Acetate → 5-Bromo-4-cyclopropyl-1(3H)-isobenzofuranone

HRID 2175884Notes

Reaction equation

HRID 2175884 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[CH:12]=[CH2:13].[CH3:14]COC(C)=O>CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[CH:12]1[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 66643955HCID 66643955, compound

Product 1

HCID 666439405-Bromo-4-cyclopropyl-1(3H)-isobenzofuranone

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a cooled (0° C.) mixture of 5-bromo-4-vinyl-2-benzofuran-1(3H)-one (2.2 g, 9.21 mol) and Pd(OAc)2 (100 mg) in EtOAc (50 mL) was added a solution of CH2N2 in ether (100 mL) slowly. The resulting mixture was stirred at room temperature overnight, then quenched with acetic acid, filtered and the filtrate washed with water and brine, dried and concentrated to provide the title compound.

Workup

  1. temperatureTo a cooled
  2. customquenched with acetic acid
  3. filtrationfiltered
  4. washthe filtrate washed with water and brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c93600b740164964883e89d4a41d5ad4
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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