Phosphorus oxychloride → 5-Benzylthiophene-2-sulfonyl chloride

HRID 2270635Notes

Reaction equation

HRID 2270635 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[CH2:7]([C:14]1[S:18][C:17]([S:19]([OH:22])(=O)=[O:20])=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.P(Cl)(Cl)([Cl:25])=O>>[CH2:7]([C:14]1[S:18][C:17]([S:19]([Cl:25])(=[O:22])=[O:20])=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 22998500HCID 22998500, compound

Product 1

HCID 134257165-Benzylthiophene-2-sulfonyl chlorideYield 39%

Procedure

Phosphorous pentachloride (2.08 g, 40 mmol) was added to a solution of 5-benzylthiophene-2-sulfonic acid in phosphorous oxychloride (6.0 g, 40 mmol) at 0° C. The reaction mixture was kept at 50° C. for 1 h, cooled to room temperature, then poured onto crushed ice (50 g) and extracted with ethyl acetate (2×30 ml). Removal of the solvent under reduced pressure gave a crude product, which was purified by column chromatography using 3% ethyl acetate in hexane to give 2-benzylthiophene-5-sulfonyl chloride (0.6 g, 39% yield).

Workup

  1. additionpoured
  2. extractionextracted with ethyl acetate (2×30 ml)
  3. customRemoval of the solvent under reduced pressure
  4. customgave a crude product, which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-f775f0b0443748798923d4cddc1a82e2
Source dataset
uspto-grants-2001_12
Patent number
US06331637B1

Reaction notes

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