m-Chloroperbenzoic acid → 4-fluoro-5-(oxiran-2-yl)-3H-2-benzofuran-1-one

HRID 1848524Notes

Reaction equation

HRID 1848524 reaction equation
[F:1][C:2]1[C:10]([CH:11]=[CH2:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:13].C1C=C(Cl)C=C(C(OO)=[O:22])C=1>C(Cl)Cl>[F:1][C:2]1[C:10]([CH:11]2[CH2:12][O:22]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 666441764-fluoro-5-vinyl-3H-isobenzofuran-1-one

Product 1

HCID 595686724-fluoro-5-(oxiran-2-yl)-3H-2-benzofuran-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-fluoro-5-vinyl-3H-isobenzofuran-1-one (4.0 g, 17.3 mmol) in 100 mL of DCM was slowly added mCPBA (6.0 g, 85% purity, 34.6 mmol) in 50 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 were washed with brine and then concentrated. The residue was purified by column chromatography to give 4-fluoro-5-oxiranyl-3H-isobenzofuran-1-one. 1H-NMR (400 MHz, CDCl3) δ ppm 7.71 (d, J=7.8 Hz, 1H), 7.37-7.40 (m, 1H), 5.37 (s, 2H), 4.21-4.22 (m, 1H), 3.25-3.27 (m, 1H), 2.80-2.82 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-a4b1c3eac94449b8a316ceacdc9ec213
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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