m-Chloroperbenzoic acid → Methyl 2-(2-chloro-4-fluorophenyl)-3-(oxiran-2-yl)propanoate

HRID 451519Notes

Reaction equation

HRID 451519 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:14][CH:15]=[CH2:16])[C:10]([O:12][CH3:13])=[O:11].ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:14][CH:15]1[CH2:16][O:25]1)[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67342147Methyl 2-(2-chloro-4-fluorophenyl)pent-4-enoate

Product 1

HCID 86656715Methyl 2-(2-chloro-4-fluorophenyl)-3-(oxiran-2-yl)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of methyl 2-(2-chloro-4-fluorophenyl)pent-4-enoate (6.0 g, 24.7 mmol) in methylene chloride (50 mL) was added meta-chloroperbenzoic acid (6.7 g, 70% purity, 27.2 mmol). The cooling bath removed and the reaction stirred for 16 hours. The reaction was filtered, the filtrate washed repeatedly with 1 N sodium hydroxide, dried with sodium sulfate and the solvent was evaporated in vacuo. The residue was purified by column chromatography on silica gel using n-heptane/ethyl acetate (v/v 1:9 to 2:8) as eluent. The title compound was obtained as a colourless liquid (5.1 g, 80%).

Workup

  1. customThe cooling bath removed
  2. filtrationThe reaction was filtered
  3. washthe filtrate washed repeatedly with 1 N sodium hydroxide
  4. dry with materialdried with sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-876cf1e758fc4ed8bc107abda291739e
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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