Water → 1,2,4-Trifluoro-5-methanesulfinyl-benzene

HRID 2066854Notes

Reaction equation

HRID 2066854 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[F:12][C:13]1[CH:18]=[C:17]([S:19][CH3:20])[C:16]([F:21])=[CH:15][C:14]=1[F:22].[OH2:23]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[F:12][C:13]1[CH:18]=[C:17]([S:19]([CH3:20])=[O:9])[C:16]([F:21])=[CH:15][C:14]=1[F:22].[F:12][C:13]1[CH:18]=[C:17]([S:19]([CH3:20])(=[O:9])=[O:23])[C:16]([F:21])=[CH:15][C:14]=1[F:22]

Participants

7

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 467394612,4,5-Trifluorothioanisole

Product 2

HCID 467393961,2,4-Trifluoro-5-(methylsulfonyl)benzeneYield 14%HCID 673085031,2,4-Trifluoro-5-methanesulfinyl-benzeneYield 24%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

MCPBA (4.93 g, 22 mmol) in DCM (20 mL) was added to an ice cooled solution of 43a (22 mmol) in DCM (40 mL). After 2 h, the mixture was diluted with water (30 mL) and saturated NaHCO3 (30 mL) and stirred for 20 minutes. The organic layer was removed and the aqueous layer was extracted with DCM (2×20 mL). The combined organic extracts were dried and concentrated. The residue was purified by flash LC(10 to 40% EtOAc+0.1% triethylamine in hexane) to afford 1,2,4-trifluoro-5-methanesulfinyl-benzene 43b (0.41 g, 24% yield, HPLC, LC-MS 195.0 (MH)) and 1,2,4-trifluoro-5-methanesulfonyl-benzene 43c (0.63 g, 14%) as white powders.

Workup

  1. customThe organic layer was removed
  2. extractionthe aqueous layer was extracted with DCM (2×20 mL)
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customThe residue was purified by flash LC(10 to 40% EtOAc+0.1% triethylamine in hexane)

Sources & evidence

ORD record
ord-7bcaf7230a314be98cb59779fd5f5fe0
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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