m-Chloroperbenzoic acid → HCID 19010447, compound

HRID 1741591Notes

Reaction equation

HRID 1741591 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[F:12][C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=1)[O:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1.S([O-])(O)=O.[Na+]>C(Cl)Cl>[F:12][C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=1)[O:16][C:17]1[CH:18]=[N+:19]([O-:9])[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 126734843-(3-Fluorophenoxy)pyridineHCID 23665763Sodium Bisulfite

Product 1

HCID 19010447HCID 19010447, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 46.3 g of m-chloroperbenzoic acid in 460 ml of methylene chloride, 37.35 g of 3-(3-fluorophenoxy)pyridine was added at room temperature, and the mixture was stirred at room temperature for 1.5 hours. An aqueous sodium hydrogen sulfite solution (20%, 120 ml) was added to the mixture and then the mixture was stirred for a few minutes. The organic layer separated was washed with 10% aqueous sodium hydroxide solution and with water, dried over anhydrous sodium sulfate, and concentrated. The residue was crystallized by trituration with isopropyl ether. The crystals were collected by filtration and washed with isopropyl ether to yield 34.44 g of pale yellow crystals, which were recrystallized from ethyl acetate to give colorless needles, mp 59°-61° C.

Workup

  1. stirringthe mixture was stirred for a few minutes
  2. customThe organic layer separated
  3. washwas washed with 10% aqueous sodium hydroxide solution and with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was crystallized by trituration with isopropyl ether
  7. filtrationThe crystals were collected by filtration
  8. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-d0d03700173f4b0e977ff52aae7f3d10
Source dataset
uspto-grants-1994_08
Patent number
US05334594

Reaction notes

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