m-Chloroperbenzoic acid → HCID 67163938, compound

HRID 552487Notes

Reaction equation

HRID 552487 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([CH3:14])[CH:9]=2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:23])C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N+:11]([O-:23])=[C:10]([CH3:14])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 17888045HCID 17888045, compound

Product 1

HCID 67163938HCID 67163938, compoundYield 203%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.50 g (8.0 mmol) of 4-(4-Fluoro-phenyl)-2-methyl-pyridine in 25 ml of methylene chloride were added 5.93 g (24 mmol, 3.0 equiv.) of 70% m-Chloroperbenzoic acid. The reaction was stirred for 6 h at room temperature. The reaction was worked up with 50 ml 5% sodium bicarbonate solution. The aqueous phase was extracted twice with 40 ml of methylene chloride. The combined organic phases were washed with 30 ml of brine, dried over magnesium sulfate, and concentrated in vaccuo to yield 3.3 g of a yellow oil which was purified by flash chromatography (ethyl acetate/methanol 9:1) to yield the title compound (1.31 g, 80%) as a crystalline light brown solid, MS (ISP): m/e=204.1 (M+H)+.

Workup

  1. extractionThe aqueous phase was extracted twice with 40 ml of methylene chloride
  2. washThe combined organic phases were washed with 30 ml of brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vaccuo

Sources & evidence

ORD record
ord-c1a73db7bbcb4c51a3beed2a4833cdef
Source dataset
uspto-grants-2011_05
Patent number
US07951824B2

Reaction notes

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