m-Chloroperbenzoic acid → 5-Fluoro-2-(methylsulfinyl)benzo[d]thiazole

HRID 220375Notes

Reaction equation

HRID 220375 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10][CH3:11])=[N:7][C:6]=2[CH:12]=1.C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([CH3:11])=[O:21])=[N:7][C:6]=2[CH:12]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 552527075-Fluoro-2-(methylthio)benzo[d]thiazole

Product 1

HCID 581806265-Fluoro-2-(methylsulfinyl)benzo[d]thiazoleYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Fluoro-2-(methylthio)benzo[d]thiazole (example 40A, 0.178 g, 0.893 mmol) was dissolved in CH2Cl2 (5.96 mL). mCPBA (0.154 g, 0.893 mmol) was added in one portion and the reaction mixture was stirred at room temperature. The reaction was quenched with saturated aqueous sodium bicarbonate and diluted with dichloromethane. The aqueous layer was extracted with dichloromethane (2×). The combined organic were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. 5-Fluoro-2-(methylsulfinyl)benzo[d]thiazole (0.180 g, 94% yield) was isolated as a white solid and used without further purification.

Workup

  1. customThe reaction was quenched with saturated aqueous sodium bicarbonate
  2. additiondiluted with dichloromethane
  3. extractionThe aqueous layer was extracted with dichloromethane (2×)
  4. washThe combined organic were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1dd7785dc7894c8eb5d0e4b0abe7bb10
Source dataset
uspto-grants-2012_06
Patent number
US08202881B2

Reaction notes

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