m-Chloroperbenzoic acid → HCID 23114642, compound

HRID 2080397Notes

Reaction equation

HRID 2080397 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]([S:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[F:16].ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]([S:17]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=[O:33])[C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[F:16]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 231146243-Chloro-4-{[(4-chlorophenyl)sulfanyl](2,5-difluorophenyl)methyl}pyridine

Product 1

HCID 23114642HCID 23114642, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride (10 ml) solution of the 3-chloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine (75 mg, 0.20 mmol) obtained in Example 53 was added 3-chloroperbenzoic acid (33 mg, 0.20 mmol). Under ice cooling, the resulting mixture was stirred for 3 hours. After dilution with ether (80 ml), the diluted mixture was washed with water and brine and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=3:1) to give the title compound (48 mg, 60%) as a diastereomer mixture (1:1).

Workup

  1. washAfter dilution with ether (80 ml), the diluted mixture was washed with water and brine
  2. concentrationconcentrated under reduced pressure
  3. customThe residue thus obtained
  4. customwas purified by silica gel chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-5b5da7bde35541c28f2bcb4fbfac930b
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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