m-Chloroperbenzoic acid → HCID 86223896, compound

HRID 2387014Notes

Reaction equation

HRID 2387014 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[F:12][C:13]([F:27])([F:26])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][C:22]([F:25])([F:24])[F:23])[N:16]=1>C(Cl)(Cl)Cl>[F:27][C:13]([F:12])([F:26])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][C:22]([F:25])([F:24])[F:23])[N+:16]=1[O-:6]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18920659HCID 18920659, compound

Product 1

HCID 86223896HCID 86223896, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Chloroperoxybenzoic acid (4.52 g, 26.2 mmol) was added to a solution of 2,6-bis-(2,2,2-trifluoro-ethyl)-pyridine (4.25 g, 17.5 mmol) in CHCl3 (70 mL). The reaction was stirred at room temperature for 4 hours and then quenched with satd Na2SO3. The layers were separated and the aqueous layer was extracted with CH2Cl2. The organic layers were washed with 1 N NaOH, brine, dried over Na2SO4 and concentrated to a yellow oil. Purification by flash column chromatography (0% to 50% EtOAc in hexanes) gave the product as a yellow solid (2.65 g, 58%). 1H NMR (400 MHz, CDCl3): δ 3.96 (q, J=10.4 Hz, 4 H), 7.27 (t, J=8.1 Hz, 1 H), 7.47 (d, J=8.1 Hz, 2H).

Workup

  1. customquenched with satd Na2SO3
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washThe organic layers were washed with 1 N NaOH, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to a yellow oil
  7. customPurification by flash column chromatography (0% to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-fd2e49f883e148cd914d7e40a780e9cf
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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