m-Chloroperbenzoic acid → 4-(4-Bromo-2-ethylphenyl)-2,2,6,6-tetramethyl-1-oxo-dihydrothiopyran-3,5-dione

HRID 341674Notes

Reaction equation

HRID 341674 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[C:24](=[O:25])[C:23]([CH3:27])([CH3:26])[S:22][C:21]([CH3:29])([CH3:28])[C:20]2=[O:30])=[C:15]([CH2:31][CH3:32])[CH:14]=1>ClCCl.O>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[C:24](=[O:25])[C:23]([CH3:26])([CH3:27])[S:22](=[O:9])[C:21]([CH3:29])([CH3:28])[C:20]2=[O:30])=[C:15]([CH2:31][CH3:32])[CH:14]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 687330264-(4-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylthiopyran-3,5-dione

Product 1

HCID 687336794-(4-Bromo-2-ethylphenyl)-2,2,6,6-tetramethyl-1-oxo-dihydrothiopyran-3,5-dioneYield 54.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3-chloroperbenzoic acid (2.45 g, 0.0142 mol) in dichloromethane (40 ml) is added to a pre-cooled solution (0° C.) of 4-(4-bromo-2-ethylphenyl)-2,2,6,6-tetramethyl-thiopyran-3,5-dione (3.5 g, 0.0095 mol) in dichloromethane (100 ml). The reaction mixture is stirred at 0° C. for one hour and then allowed to come to room temperature. The reaction mixture is stirred at room temperature for one hour, diluted with water (100 ml) and separated. The organic phase is collected, and the aqueous layer is extracted with dichloromethane (2×50 ml). The organic phases are combined, washed with water, and dried over anhydrous sodium sulfate. The mixture is filtered, and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 4-(4-bromo-2-ethylphenyl)-2,2,6,6-tetramethyl-1-oxo-dihydrothiopyran-3,5-dione as a white solid (2.0 g).

Workup

  1. customto come to room temperature
  2. stirringThe reaction mixture is stirred at room temperature for one hour
  3. customseparated
  4. customThe organic phase is collected
  5. extractionthe aqueous layer is extracted with dichloromethane (2×50 ml)
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe mixture is filtered
  9. customthe filtrate is evaporated under reduced pressure
  10. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-82da870b120643d081476f32c88360b2
Source dataset
uspto-grants-2014_11
Patent number
US08895761B2

Reaction notes

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