Ethyl Acetate → 2-(4-Chloro-2-methoxyphenyl)-ethenesulfonyl chloride

HRID 2283275Notes

Reaction equation

HRID 2283275 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][S:14](O)(=[O:16])=[O:15])=[C:8]([O:18][CH3:19])[CH:7]=1.C(OCC)(=O)C>CN(C=O)C>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][S:14]([Cl:3])(=[O:16])=[O:15])=[C:8]([O:18][CH3:19])[CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 866320042-(4-Chloro-2-methoxy-phenyl)-ethenesulfonic acid

Product 1

HCID 739930052-(4-Chloro-2-methoxyphenyl)-ethenesulfonyl chlorideYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thionyl chloride (8.1 mL, 111.19 mmol) was added dropwise at 0° C. to a solution of 2-(4-chloro-2-methoxy-phenyl)-ethenesulfonic acid (5.53 g, 22.24 mmol) in DMF (10 mL). The reaction mixture was stirred at RT for 3 h and then was poured onto crushed ice. Ethyl acetate (50 mL) was added to the mixture. The organic phase was separated, washed with brine (3×20 mL), dried over MgSO4 and concentrated under reduced pressure. The oily residue was purified on silica gel using hexane/ethyl acetate, 4:1 to give the target compound which was then recrystallized from pentane/diethyl ether to afford the title compound (2.30 g, 61% over 3 steps) as a white solid.

Workup

  1. additionwas poured
  2. customonto crushed ice
  3. customThe organic phase was separated
  4. washwashed with brine (3×20 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe oily residue was purified on silica gel
  8. customto give the target compound which
  9. customwas then recrystallized from pentane/diethyl ether

Sources & evidence

ORD record
ord-ddd672ad40be4aaa96862b3222fa1677
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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