Hydrogen Peroxide → 2,2-Difluoro-7-hydroxy-benzo[1,3]dioxole-5-carboxylic Acid Methyl Ester

HRID 1918374Notes

Reaction equation

HRID 1918374 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14](B2OCC(C)(C)CO2)[C:8]2[O:9][C:10]([F:13])([F:12])[O:11][C:7]=2[CH:6]=1)=[O:4].[OH:24]O>CO>[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([OH:24])[C:8]2[O:9][C:10]([F:13])([F:12])[O:11][C:7]=2[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 67170313Methyl 7-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-2,2-difluorobenzo[d][1,3]dioxole-5-carboxylate

Product 1

HCID 671699732,2-Difluoro-7-hydroxy-benzo[1,3]dioxole-5-carboxylic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.0 g of 7-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-2,2-difluoro-benzo[1,3]dioxole-5-carboxylic acid methyl ester were dissolved using 200 ml of methanol and 30 ml of a 33% aqueous solution of H2O2 added. Stirring was continued for 30 minutes at room temperature. The reaction mixture was then concentrated to 20 ml and 100 ml of water and 100 ml of a saturated aqueous NaCl-solution added. The reaction mixture was then extracted three times using 100 ml of CH2Cl2 each, dried using MgSO4, and evaporated. Chromatography on silica gel using EA/HEP 1:4 yielded 1.8 g of the title compound, colorless oil.

Workup

  1. additionadded
  2. concentrationThe reaction mixture was then concentrated to 20 ml and 100 ml of water and 100 ml of a saturated aqueous NaCl-solution
  3. additionadded
  4. extractionThe reaction mixture was then extracted three times
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-c499ed99b6884ae2bc62515c7a5b7fc8
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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