Potassium Carbonate → Ethyl 4,5-dichloro-1,3-benzodioxole-2-carboxylate

HRID 1074188Notes

Reaction equation

HRID 1074188 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[C:4]([OH:9])[C:3]=1[OH:10].C(=O)([O-])[O-].[K+].[K+].Br[CH:18](Br)[C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O>[Cl:1][C:2]1[C:3]2[O:10][CH:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[O:9][C:4]=2[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 198773,4-DichlorocatecholHCID 69237Ethyl dibromoacetate

Product 1

HCID 14748637Ethyl 4,5-dichloro-1,3-benzodioxole-2-carboxylateYield 66.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 11.0 g of 3,4-dichloro-1,2-benzenediol, 15.38 g of potassium carbonate, 27 g of ethyl dibromoacetate and 100 ml of dimethylformamide is stirred at 100° C. under argon gas atmosphere for 4 hours. The reaction mixture is evaporated to remove solvent and ethyl acetate and water is added to the residue. The organic layer is separated, washed with water, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography to give 10.75 g of ethyl 4,5-dichloro-1,3-benzodioxole-2-carboxylate.

Workup

  1. customThe reaction mixture is evaporated
  2. customto remove solvent and ethyl acetate and water
  3. additionis added to the residue
  4. customThe organic layer is separated
  5. washwashed with water
  6. customdried
  7. customevaporated
  8. customto remove solvent
  9. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3e4bd09f64d1463bb5969599b4d6b8f4
Source dataset
uspto-grants-1990_11
Patent number
US04973600

Reaction notes

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