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

HRID 1188053Notes

Reaction equation

HRID 1188053 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-b4accc5624d14c4485897e7f3236bef6
Source dataset
uspto-grants-2014_03
Patent number
US08673933B2

Reaction notes

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