m-Chloroperbenzoic acid → HCID 59766902, compound

HRID 2389711Notes

Reaction equation

HRID 2389711 reaction equation
[C:1]([O:5][C:6](=[O:47])[N:7]([CH:9]1[CH2:14][CH2:13][CH:12]([N:15]([C:33]([C:35]2[S:39][C:38]3[C:40]([F:45])=[CH:41][CH:42]=[C:43]([F:44])[C:37]=3[C:36]=2[Cl:46])=[O:34])[CH2:16][C:17]2[CH:18]=[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[S:31][CH3:32])[CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=[O:49].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl.[O-]S([O-])=O.[Na+].[Na+]>[C:1]([O:5][C:6](=[O:47])[N:7]([CH:9]1[CH2:10][CH2:11][CH:12]([N:15]([C:33]([C:35]2[S:39][C:38]3[C:40]([F:45])=[CH:41][CH:42]=[C:43]([F:44])[C:37]=3[C:36]=2[Cl:46])=[O:34])[CH2:16][C:17]2[CH:18]=[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[S:31]([CH3:32])=[O:49])[CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[CH2:13][CH2:14]1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 59766958HCID 59766958, compound

Product 1

HCID 59766902HCID 59766902, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24437Sodium SulfiteSolvent

Procedure

To a stirred suspension of thioanisole (286) (75 mg, 0.11 mmol) and NaHCO3 (46 mg, 0.55 mmol) in DCM (2 ml) at 0° C. was added dropwise a solution of m-chloroperbenzoic acid (34 mg, 0.2 mmol) in DCM (1 ml) over 2 min. After 2 h, LCMS showed a mixture of sulphoxide and sulphone. The reaction was diluted with aqueous Na2SO3 and extracted with DCM. The combined organic layers were dried (Na2SO4), filtered and reduced in vacuo before purification by chromatography with EtOAc/heptane to give the title compound.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customreduced in vacuo before purification by chromatography with EtOAc/heptane

Sources & evidence

ORD record
ord-30026abfc7ab49a481837297e0dc7140
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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