Chlorosulfonic acid → HCID 22998464, compound

HRID 1166936Notes

Reaction equation

HRID 1166936 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1.[Cl:13][S:14](O)(=[O:16])=[O:15].P(Cl)(Cl)(Cl)=O.P(Cl)(Cl)(Cl)(Cl)Cl>>[Cl:13][S:14]([C:9]1[S:8][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:12])=[CH:11][CH:10]=1)(=[O:16])=[O:15]

Participants

5

Reactant 4

HCID 24638Chlorosulfonic acidHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 35641892-(2-methylphenyl)thiophene

Product 1

HCID 22998464HCID 22998464, compoundYield 80.7%

Procedure

To the cold (−5 to 0° C.) solution of 2-(2-tolyl)thiophene (0.87 g, 5 mmole) was added chlorosulfonic acid (0.33 ml, 5 mmole) over a 15 min. period with constant stirring. After 10 min., phosphorus oxychloride (2 ml) and phosphorous pentachloride were added. The reaction mixture was slowly allowed to attain ambient temperature and stirred for 3 hours. The mixture was then poured onto crushed ice (50 g) and was extracted with ethyl acetate (2×50 ml). The combined organic layers was dried over MgSO4 and evaporated. The residue was purified by flash column chromatography on silica gel using 2% ethyl acetate in hexane to give 2-chlorosulfonyl-5-(2-tolyl)thiophene, (1.1 g, 72% yield).

Workup

  1. customto attain ambient temperature
  2. additionThe mixture was then poured
  3. extractionwas extracted with ethyl acetate (2×50 ml)
  4. dry with materialThe combined organic layers was dried over MgSO4
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on silica gel using 2% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ef2f8b1d4c1f44dcb95dbcfbfb466de0
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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