m-Chloroperbenzoic acid → 2-(4-Methoxybenzoyl)-3-phenylbenzothiophene-1-oxide

HRID 616626Notes

Reaction equation

HRID 616626 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([C:7]([C:9]2[S:10][C:11]3[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=3[C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:8])=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:34])C=1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([C:9]2[S:10](=[O:34])[C:11]3[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=3[C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:8])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 154064042-(4-Methoxybenzoyl)-3-phenylbenzothiophene

Product 1

HCID 203683422-(4-Methoxybenzoyl)-3-phenylbenzothiophene-1-oxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The product from Example 1 (8.2 g,; 0.0238 mole) dissolved in chloroform was cooled in an ice-ethanol bath, and 4.5 g. (0.026 mole) of m-chloroperbenzoic acid in chloroform were added dropwise. The mixture was stirred at room temperature overnight. The resulting mixture then was washed successively with aqueous sodium bicarbonate solution, aqueous sodium chloride solution, and water. The mixture then was dried over magnesium sulfate. The mixture was concentrated, and ethanol was added to the residue. The product crystallized upon scratching of the vessel wall. The solid was filtered and washed with a mixture of ethanol and ether. The solid was air dried to obtain 7.2 g. of product, m.p. 118°-120° C. Thin layer chromatography (TLC) showed the presence of a trace of starting material.

Workup

  1. temperaturewas cooled in an ice-ethanol bath
  2. washThe resulting mixture then was washed successively with aqueous sodium bicarbonate solution, aqueous sodium chloride solution, and water
  3. dry with materialThe mixture then was dried over magnesium sulfate
  4. concentrationThe mixture was concentrated
  5. additionethanol was added to the residue
  6. customThe product crystallized
  7. filtrationThe solid was filtered
  8. washwashed with a mixture of ethanol and ether
  9. customdried
  10. customto obtain 7.2 g

Sources & evidence

ORD record
ord-7db3fefd718b496d9e7f1c2f8b1408e5
Source dataset
uspto-grants-1978_02
Patent number
US04075227

Reaction notes

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