m-Chloroperbenzoic acid → HCID 59568686, compound

HRID 1187074Notes

Reaction equation

HRID 1187074 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[F:12][C:13]1[C:18]2[C:19](=[O:22])[O:20][CH2:21][C:17]=2[CH:16]=[C:15]([CH:23]=[CH2:24])[CH:14]=1>C(Cl)Cl>[F:12][C:13]1[C:18]2[C:19](=[O:22])[O:20][CH2:21][C:17]=2[CH:16]=[C:15]([CH:23]2[CH2:24][O:9]2)[CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 666439945-Ethenyl-7-fluoro-1(3H)-isobenzofuranone

Product 1

HCID 59568686HCID 59568686, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mCPBA (85%, 9.9 g, 48.9 mmol) was added to a solution of 7-fluoro-5-vinyl-2-benzofuran-1(3H)-one (2.9 g, 16.3 mmol) in 300 mL of DCM at 0° C. The mixture was stirred at room temperature for 16 hours before being cooled to 0° C. The mixture was washed sequentially with saturated NaHCO3 (50 mL), aqueous Na2SO3 (50 mL×2), 5% NaOH (50 mL) and brine, then concentrated. The residue was purified by column chromatography eluted with DCM to afford 7-fluoro-5-oxiran-2-yl-2-benzofuran-1(3H)-one as white solid.

Workup

  1. temperaturebefore being cooled to 0° C
  2. washThe mixture was washed sequentially with saturated NaHCO3 (50 mL), aqueous Na2SO3 (50 mL×2), 5% NaOH (50 mL) and brine
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography
  5. washeluted with DCM

Sources & evidence

ORD record
ord-c8dc39f7628b47b9a2eb6806153f488c
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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