m-Chloroperbenzoic acid → HCID 58807658, compound

HRID 1367119Notes

Reaction equation

HRID 1367119 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([P:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:10]2[C:15]([CH3:16])=[CH:14][C:13]([Br:17])=[C:12]([CH3:18])[CH:11]=2)=[CH:4][C:3]=1[CH3:25].ClC1C=C(C=CC=1)C(OO)=[O:31]>C(Cl)Cl>[Br:17][C:13]1[CH:14]=[C:15]([CH3:16])[C:10]([P:9](=[O:31])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]2[C:6]([CH3:8])=[CH:7][C:2]([Br:1])=[C:3]([CH3:25])[CH:4]=2)=[CH:11][C:12]=1[CH3:18]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58807659HCID 58807659, compound

Product 1

HCID 58807658HCID 58807658, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Monomer 1 (30 g, 63.0 mmol, 1 equiv.) was dissolved in methylene choride (200 ml) at room temperature. m-Chloroperoxybenzoic acid (MCPBA, 50 wt %, ca. 22 g, 63.0 mmol, 1 equiv) was then added portion wise. A small exotherm was noted. Once the addition was complete, thin layer chromatography revealed complete conversion after approximately 5 minutes. The crude product was extracted with aqueous sodium hydroxide (2 M) and the organic layer evaporated under reduced pressure to give the crude product as a white solid. Crystallisation from ethanol gave the title compound (19 g, 63%). GC-MS 99.6%, M+ 491 (expected M+ 491)); 31P-NMR (CDCl3) δ (ppm) 34.

Workup

  1. additionOnce the addition
  2. customafter approximately 5 minutes
  3. extractionThe crude product was extracted with aqueous sodium hydroxide (2 M)
  4. customthe organic layer evaporated under reduced pressure
  5. customto give the crude product as a white solid
  6. customCrystallisation from ethanol

Sources & evidence

ORD record
ord-38cdeb91ad8448599c9b260e0ec2f94f
Source dataset
uspto-grants-2011_02
Patent number
US07893172B2

Reaction notes

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