Chlorosulfonic acid → 5-Chlorofuran-2-sulfonyl chloride

HRID 640046Notes

Reaction equation

HRID 640046 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[Cl:7][S:8]([OH:11])(=O)=[O:9].[Cl:12][C:13]1[O:14][CH:15]=[CH:16][CH:17]=1>>[Cl:12][C:13]1[O:14][C:15]([S:8]([Cl:7])(=[O:11])=[O:9])=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 24638Chlorosulfonic acidHCID 24819Phosphorus pentachlorideHCID 1378562-Chlorofuran

Product 1

HCID 225007325-Chlorofuran-2-sulfonyl chlorideYield 36.02%

Conditions

Temperature
25 °C

Procedure

Phosphorus pentachloride (40.53 g, 0.1947 mol) was added portionwise (caution, foaming) over 5 min at 25° C. to chlorosulfonic acid (56.8 g, 32.4 mL, 0.487 mol) and the resulting solution was stirred at 25° C. for 10 min. Then, 2-chlorofuran (20.0 g, 20 0.1947 mol) was added in one portion and the resulting dark suspension was heated to 55° C. for 1.0 h during which time foaming occurred and subsided. The reaction mixture was then poured onto ice and the resulting suspension was extracted with CH2Cl2 (250 mL). The organic was filtered through a pad of celite, washed with brine (70 mL) and dried over MgSO4. The solvent was removed in vacuo to provide 5-chlorofuran-2-sulfonyl chloride as a black oil (14.1 g, 36.02%). 1H-NMR (DMSO-d6, 400 MHz) δ 7.05 (d, 1H); 6.35 (d, 1 H).

Workup

  1. temperaturethe resulting dark suspension was heated to 55° C. for 1.0 h during which time
  2. additionThe reaction mixture was then poured onto ice
  3. extractionthe resulting suspension was extracted with CH2Cl2 (250 mL)
  4. filtrationThe organic was filtered through a pad of celite
  5. washwashed with brine (70 mL)
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-327a3fd7be35407abbc34ec766cc6f23
Source dataset
uspto-grants-2010_04
Patent number
US07691884B2

Reaction notes

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