Bromine → 5,6-Dimethyl-2-benzofuran-1,3-dione

HRID 2111613Notes

Reaction equation

HRID 2111613 reaction equation
[CH3:1][C:2]1[CH2:3][CH:4]2[C:8](=[O:9])[O:7][C:6](=[O:10])[CH:5]2[CH2:11][C:12]=1[CH3:13].BrBr>C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[O:9])[O:7][C:6](=[O:10])[C:5]2=[CH:11][C:12]=1[CH3:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 2262975,6-Dimethyl-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione

Product 1

HCID 2266445,6-Dimethyl-2-benzofuran-1,3-dioneYield 37.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of above-mentioned (a) (9.5 g, 53 mmol) in acetic acid (28 ml) was added dropwise a solution of bromine (6.1 ml, 0.12 mol) in acetic acid (28 ml) at 115° C. over a period of 45 minutes, and heated under reflux for 1 hr. The reaction solution was left overnight, and the precipitated crystals were collected by filtration, washed with diethyl ether, followed by drying to give 3.5 g of the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hr
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with diethyl ether
  5. customby drying

Sources & evidence

ORD record
ord-775a5915e0134962b64571b7a3ad06c5
Source dataset
uspto-grants-2009_04
Patent number
US07521451B2

Reaction notes

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