m-Chloroperbenzoic acid → HCID 59568716, compound

HRID 1474337Notes

Reaction equation

HRID 1474337 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH2:14])[C:5]([CH3:12])=[C:6]2[C:10]=1[C:9](=[O:11])[O:8][CH2:7]2.C1C=C(Cl)C=C(C(OO)=[O:23])C=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:13]2[CH2:14][O:23]2)[C:5]([CH3:12])=[C:6]2[C:10]=1[C:9](=[O:11])[O:8][CH2:7]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66643889HCID 66643889, compound

Product 1

HCID 59568716HCID 59568716, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7-fluoro-4-methyl-5-vinyl-3H-isobenzofuran-1-one (420 mg, 1.71 mmol) in 10 mL of DCM was slowly added mCPBA (741 mg, 85% purity, 3.43 mmol) in 10 mL of DCM at 0° C. After warming to room temperature, the mixture was stirred overnight. The mixture was washed with aqueous Na2SO3 until KI paper didn't change color. The organic layers was washed with brine and then concentrated. The residue was purified by column chromatography to give product 7-fluoro-4-methyl-5-oxiranyl-3H-isobenzofuran-1-one. The enantiomers of the product were resolved via SFC (Column Chiralpak AD-H 250*4.6 mm I.D., 5 μm; Mobile phase: methanol (0.05% DEA) in CO2 from 5% to 40%; Flow rate: 2.35 mL/min; Wavelength: 220 nm). MS m/z 209 (M+1)+.

Workup

  1. customat 0° C
  2. washThe mixture was washed with aqueous Na2SO3 until KI paper didn't change color
  3. washThe organic layers was washed with brine
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2efc60ce1c89433da3c4017f284556af
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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