Water → 2-(2-Fluoro-5-nitrophenyl)-2-methyloxirane

HRID 1963741Notes

Reaction equation

HRID 1963741 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([CH3:13])=[CH2:12].O.C1C=C(Cl)C=C(C(OO)=[O:23])C=1>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1([CH3:13])[CH2:12][O:23]1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 600980171-Fluoro-4-nitro-2-(prop-1-en-2-yl)benzene

Product 1

HCID 860454042-(2-Fluoro-5-nitrophenyl)-2-methyloxirane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
10 °C

Procedure

1-fluoro-4-nitro-2-(prop-1-en-2-yl)benzene (1 eq) was dissolved in dichloromethane and cooled to 10° C. using and ice/salt/water bath under nitrogen. MCPBA (1.5 eq) in dichloromethane was then added dropwise and resulting solution allowed to warm to room temperature and allowed to stir 48 h. Solution was quenched with 10% sodium sulfite, neutralized with saturated solution of sodium bicarbonate, extracted with dichloromethane. Organics were washed with brine, dried with sodium sulfate and concentrated. Crude product was purified with flash chromatography (85% Hex:15% EtoAc) to afford 2-(2-fluoro-5-nitrophenyl)-2-methyloxirane.

Workup

  1. customresulting solution
  2. temperatureto warm to room temperature
  3. customSolution was quenched with 10% sodium sulfite
  4. extractionextracted with dichloromethane
  5. washOrganics were washed with brine
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated
  8. customCrude product was purified with flash chromatography (85% Hex:15% EtoAc)

Sources & evidence

ORD record
ord-f5460a291c134f30b5303b9d0c1505a9
Source dataset
uspto-grants-2013_04
Patent number
US08415382B2

Reaction notes

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