m-Chloroperbenzoic acid → HCID 59853076, compound

HRID 2374053Notes

Reaction equation

HRID 2374053 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][S:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:24])C=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][S:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:24])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 20542843HCID 20542843, compound

Product 1

HCID 59853076HCID 59853076, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 2-(4-fluorobenzylthio)acetate (1.89 g, 8.29 mmol) in DCM (20.0 mL) at −40° C. was added a solution of m-CPBA (77%, 1.86 g, 8.29 mmol) in DCM (20.0 mL) dropwise. The solution was stirred from −40° C. to room temperature overnight. The solution was then quenched with polymer bound diethylene triamine. After filtration and concentration, the residue was purified by flash chromatography on SiO2 to give ethyl 2-(4-fluorobenzylsulfinyl)acetate (2.0 g, 98% yield). MS(ESI+): m/z 267.09 (M+H)+.

Workup

  1. customThe solution was then quenched with polymer
  2. filtrationAfter filtration and concentration
  3. customthe residue was purified by flash chromatography on SiO2

Sources & evidence

ORD record
ord-79d8415f10194ad3b8907d8e38814b47
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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