Chloride → methyl 4-chloro-3-(chlorosulfonyl)benzoate

HRID 1845147Notes

Reaction equation

HRID 1845147 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:11]([Cl:14])(=[O:13])=[O:12].[Cl-].[CH3:16]O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:16])=[O:7])=[CH:4][C:3]=1[S:11]([Cl:14])(=[O:12])=[O:13]

Participants

4

Reactant 3

HCID 312ChlorideHCID 887MethanolHCID 756134-Chloro-3-(chlorosulphonyl)benzoic acid

Product 1

HCID 18071846methyl 4-chloro-3-(chlorosulfonyl)benzoate

Procedure

A round bottom flask was charged with 4-chloro-3-(chlorosulfonyl)benzoic acid (16.0 g, 63.24 mmol) and methanol (100 mL), and thinoyl chloride (9.3 mL, 126.5 mmol) was added slowly at 0° C. The reaction mixture was then heated to reflux for 1.5 hours. The volatiles were removed under reduced pressure, and the residue was diluted with water and extracted with EtOAc. The solvents were removed under reduced pressure to get the title compound as a solid.

Workup

  1. additionwas added slowly at 0° C
  2. temperatureThe reaction mixture was then heated
  3. temperatureto reflux for 1.5 hours
  4. customThe volatiles were removed under reduced pressure
  5. additionthe residue was diluted with water
  6. extractionextracted with EtOAc
  7. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-6f0667ae0f104694bb887cc47f59ed7c
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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