Dibromomethane → Methyl 3,4-methylenedioxy-5-methoxybenzoate

HRID 2120906Notes

Reaction equation

HRID 2120906 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:13][CH3:14])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[F-].[K+].Br[CH2:18]Br.C(OCC)(=O)C.CCCCCC>CN(C)C=O>[CH3:14][O:13][C:10]1[C:11]2[O:12][CH2:18][O:1][C:2]=2[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=1

Participants

6

Reactant 4

HCID 3024DibromomethaneHCID 99622m3OMGHCID 522689Potassium FluorideHCID 21226206Ethyl acetate hexane

Product 1

HCID 601780Methyl 3,4-methylenedioxy-5-methoxybenzoateYield 59.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 3,4-dihydroxy-5-methoxybenzoate(48 g, 240 mmol) prepared in Step 2 was dissolved in dimethylformamide(1.2 l), potassium fluoride (42 g, 720 mmol) and dibromomethane(42.0 g, 480 mmol) were added thereto, and the mixture was heated while stirring for 8 hours at 80° C. The reaction solution was cooled down to room temperature and the excess solvent was removed. The residue was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, concentrated and then subjected to silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3, v/v) to give methyl 7-methoxybenzo [3,4-d]1,3-dioxolan-5-carboxylate(30 g, Yield 59%) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe reaction solution was cooled down to room temperature
  3. customthe excess solvent was removed
  4. extractionThe residue was extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e6f8bd30a4a0464c903ce95226258ed6
Source dataset
uspto-grants-2004_02
Patent number
US06693126B2

Reaction notes

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