m-Chloroperbenzoic acid → HCID 89619084, compound

HRID 1502062Notes

Reaction equation

HRID 1502062 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]2=[N:7][O:8][N:9]=[C:5]2[C:4]=1[CH3:12])=[CH2:2].C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)Cl>[CH3:12][C:4]1[C:5]2[C:6](=[N:7][O:8][N:9]=2)[CH:10]=[CH:11][C:3]=1[CH:1]1[CH2:2][O:21]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 89619523HCID 89619523, compound

Product 1

HCID 89619084HCID 89619084, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-ethenyl-4-methyl-2,1,3-benzoxadiazole (1.4 g, 8.4 mmol) and mCPBA (85%, 2.57 g, 12.6 mmol) in 200 mL of DCM was stirred at room temperature for 96 hours. The reaction mixture was cooled to 0° C. and was washed subsequently with saturated NaHCO3 (50 mL), saturated Na2SO3 (50 mL), 5% NaOH (50 mL×2) and brine (50 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica column chromatography (PE:EtOAc=5:1) to afford the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. washwas washed subsequently with saturated NaHCO3 (50 mL), saturated Na2SO3 (50 mL), 5% NaOH (50 mL×2) and brine (50 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica column chromatography (PE:EtOAc=5:1)

Sources & evidence

ORD record
ord-da13a5c6e6a84cf5a04a6356a0d8f58d
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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