m-Chloroperbenzoic acid → HCID 86680833, compound

HRID 2401689Notes

Reaction equation

HRID 2401689 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[CH:12]=1.ClC1C=CC=C(C(OO)=[O:29])C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:29])[CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][C:11]=2[CH:12]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86680832HCID 86680832, compound

Product 1

HCID 86680833HCID 86680833, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 0.38 g of 3-chloro-4-[5-(trifluoromethyl)benzofuran-2-yl]pyridine and 4 ml of chloroform was added 0.41 g of 70% m-chloroperbenzoic acid under ice-cooling. This mixture was stirred under ice-cooling for 30 minutes and subsequently at room temperature for 2 hours. The reaction mixture was diluted with chloroform, and sequentially washed with a 5% aqueous solution of sodium hydroxide and saturated brine. The organic layer was dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.32 g of 3-chloro-4-[5-(trifluoromethyl)benzofuran-2-yl]pyridine 1-oxide (hereinafter, referred to as “Present Active Compound 7”).

Workup

  1. temperaturecooling
  2. washsequentially washed with a 5% aqueous solution of sodium hydroxide and saturated brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bce3640abf324a4492acab36dbcc7787
Source dataset
uspto-grants-2014_08
Patent number
US08796306B2

Reaction notes

Loading…