Chlorosulfonic acid → 2-Thiophenesulfonyl chloride

HRID 2053058Notes

Reaction equation

HRID 2053058 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].CO[C:8]1[CH:12]=[CH:11][S:10][CH:9]=1>C(Cl)Cl>[S:10]1[CH:11]=[CH:12][CH:8]=[C:9]1[S:2]([Cl:1])(=[O:5])=[O:3]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 1402493-Methoxythiophene

Product 1

HCID 855182-Thiophenesulfonyl chlorideYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred 300 mL CH2Cl2 solution in a −78° C. cooling bath was added chlorosulfonic acid (14.5 mL, 217.8 mmol). A solution of 3-methoxythiophene (10.0 g, 87.59 mmol) in 80 mL of CH2Cl2 was added slowly along the side wall of the flask. After 30 min, the cooling bath was removed. Reaction was continued at room temperature for 2 h. Stirring was stopped, the mixture was set still for approximately 10 min, and filtered directly and carefully through a 2-in silica gel pad. The green glue residue was extracted several times with CH2Cl2 and filtered. The filtrate was concentrated under reduced pressure to afford 10.75 g (58%) of thiophene-sulfonyl chloride as an off-white (trace green-grey) solid.

Workup

  1. customthe cooling bath was removed
  2. customReaction
  3. waitwas continued at room temperature for 2 h
  4. waitthe mixture was set still for approximately 10 min
  5. filtrationfiltered directly
  6. extractionThe green glue residue was extracted several times with CH2Cl2
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-528c0e64e53b49db9df1980487e619b6
Source dataset
uspto-grants-2008_02
Patent number
US07326729B2

Reaction notes

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