m-Chloroperbenzoic acid → HCID 89618828, compound

HRID 1502088Notes

Reaction equation

HRID 1502088 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]=[CH2:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)Cl>[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[CH:4][CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:9][O:21]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 1285309384385-64-8

Product 1

HCID 89618828HCID 89618828, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Methyl-1-nitro-3-vinylbenzene (2 g, 12.26 mmol) was dissolved in DCM (50 ml) then cooled to 0° C. and added mCPBA (3.17 g, 14.14 mmol) then stirred at room temperature for 16 hrs. When TLC showed starting materials, more mCPBA (1.58 g, 7.07 mmol) was added. The reaction was stirred for another 16 hrs. The reaction was washed with saturated aqueous Na2S2O3, NaHCO3, brine; then dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography through a 120 g ISCO Redi-Sep column eluting with 0-20% ETOAc/hexane to yield the title compound.

Workup

  1. additionwas added
  2. stirringThe reaction was stirred for another 16 hrs
  3. washThe reaction was washed with saturated aqueous Na2S2O3, NaHCO3, brine
  4. dry with materialthen dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography through a 120 g ISCO Redi-Sep column
  8. washeluting with 0-20% ETOAc/hexane

Sources & evidence

ORD record
ord-9a09787764a04e0dbdd2275afc181cb0
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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