Potassium Carbonate → Ethyl 4,5-dichloro-6-(1-methyl-5-pyrazolylcarbonyl)-1,3-benzodioxole-2-carboxylate

HRID 1074174Notes

Reaction equation

HRID 1074174 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[C:13]([OH:15])[C:12]([OH:16])=[C:11]([Cl:17])[C:10]=2[Cl:18])=[O:8])=[CH:5][CH:4]=[N:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH:26](Br)[C:27]([O:29][CH2:30][CH3:31])=[O:28]>CN(C)C=O>[Cl:17][C:11]1[C:12]2[O:16][CH:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[O:15][C:13]=2[CH:14]=[C:9]([C:7]([C:6]2[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=2)=[O:8])[C:10]=1[Cl:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69237Ethyl dibromoacetateHCID 135986952(1-Methylpyrazol-5-yl)-(2,3-dichloro-4,5-dihydroxyphenyl)-methanone

Product 1

HCID 14748603Ethyl 4,5-dichloro-6-(1-methyl-5-pyrazolylcarbonyl)-1,3-benzodioxole-2-carboxylateYield 63.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.0 g of (1-methylpyrazol-5-yl)-(2,3-dichloro-4,5-dihydroxyphenyl)-methanone in 22 ml of dimethylformamide are added 2.12 g of powdered potassium carbonate and 3.7 g of ethyl dibromoacetate, and the mixture is stirred at 90° to 100° C. under argon gas atmosphere for 2 hours. After cooling, the mixture is poured into ice-water and the mixture is extracted with ethyl acetate. The extract is washed with an aqueous saturated sodium chloride solution, dried and evaporated to remove solvent under reduced pressure. The residue is purified by silica gel column chromatography (solvent; n-hexane-ethyl acetate) to give 1.64 g of ethyl 4,5-dichloro-6-(1-methyl-5-pyrazolylcarbonyl)-1,3-benzodioxole-2-carboxylate. Yield: 63%

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe extract is washed with an aqueous saturated sodium chloride solution
  4. customdried
  5. customevaporated
  6. customto remove solvent under reduced pressure
  7. customThe residue is purified by silica gel column chromatography (solvent; n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-5aceb34c52e349069f982b975eafe834
Source dataset
uspto-grants-1990_11
Patent number
US04973600

Reaction notes

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