Water → HCID 13688870, compound

HRID 542747Notes

Reaction equation

HRID 542747 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[CH2:6][CH:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[O:8][C:4]=2[C:3]=1[Cl:16].[Cl:17][S:18](O)(=[O:20])=[O:19].O>S(Cl)(Cl)=O>[Cl:17][S:18]([C:15]1[C:2]([Cl:1])=[C:3]([Cl:16])[C:4]2[O:8][CH:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][C:5]=2[CH:14]=1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 24638Chlorosulfonic acidHCID 12747889Ethyl 6,7-dichloro-2,3-dihydro-1-benzofuran-2-carboxylate

Product 1

HCID 13688870HCID 13688870, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

To a solution (2.5 ml) of 1 g (3.83 mmol) of ethyl 6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylate (1) in 2.5 ml of thionyl chloride is dropwise added 1.25 g of chlorosulfonic acid under ice-cooling and the mixture allowed to react at room temperature for 2 hours. The reaction mixture is poured into iced water and extracted with 60 ml of ethyl acetate. The organic layer is dried and evaporated to give about 1.4 g of ethyl 5-chlorosulfonyl-6,7-dichloro-2,3-dihydrobenzofuran-carboxylate (2) as an oil.

Workup

  1. temperaturecooling
  2. customto react at room temperature for 2 hours
  3. extractionextracted with 60 ml of ethyl acetate
  4. customThe organic layer is dried
  5. customevaporated

Sources & evidence

ORD record
ord-37357a73a99e40ab9ed484ca4239b700
Source dataset
uspto-grants-1987_04
Patent number
US04659709

Reaction notes

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