Acetic Acid → HCID 22677663, compound

HRID 1837950Notes

Reaction equation

HRID 1837950 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.OO.[OH2:16].C(O)(=[O:19])C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)(=[O:19])=[O:16])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 11356278HCID 11356278, compound

Product 1

HCID 22677663HCID 22677663, compoundYield 63%

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(4-fluorophenylthio)thiophene (1.09 g, 5.18 mmol) in acetic acid (14.3 mL) was added a 30% aqueous solution of H2O2 (1.30 mL). The reaction mixture was heated at 100° C. for 45 min, then was treated with water. The resulting suspension was extracted with CH2Cl2. The combined organic layers were washed with a saturated NaHCO3 solution, dried (MgSO4) and concentrated under reduced pressure to yield 2-[(4-fluorophenyl)sulfonyl]thiophene (0.79 g, 63%) as a white solid: TLC (hex) Rf 0.08; 1H NMR (CDCl3) δ 7.09-7.27 (m, 3H), 7.67-7.71 (m, 2H), 7.99-8.04 (m, 2H).

Workup

  1. extractionThe resulting suspension was extracted with CH2Cl2
  2. washThe combined organic layers were washed with a saturated NaHCO3 solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab82449c62cd4f96a92617fbdaf8fb12
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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