Benzoyl Peroxide → HCID 68463784, compound

HRID 502493Notes

Reaction equation

HRID 502493 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([F:17])[CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[Br:20]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([F:17])[CH:9]=2)=[O:7])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 68463862HCID 68463862, compound

Product 1

HCID 68463784HCID 68463784, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1.1 g (4.2 mmol) of 4-methyl-4′-nitro-3′-fluorobenzophenone, 0.654 g of recrystallized N-bromosuccinimide, 60 mg benzoyl peroxide, and 20 mL CCl4 were refluxed under argon for 3 hours. The hot solution was filtered through a glass sintered filter and rinsed with 20 mL of hot CCl4, until the crystals became colorless. The crystals were washed with 6 mL of cold CCl4 and the solution was concentrated under reduced pressure. The crude product was recrystallized from hexane and dried under vacuum. The resultant yield was 58%. 1H-NMR CDCl3: δ8.18 (dd, aromatic, 2H), 7.78 (d, aromatic, 2H), 7.68 (m, aromatic, 1H), 7.56 (d, aromatic, 2H), 4.57 (s, methyl, 3H). 13C-NMR: δ 192.4 (carbonyl); 156.2, 154.0, 146.7, 144.5, 144.4, 143.7, 143.6, 135.0, 133.0 130.5, 126.5, 125.5, 119.7, 119.4 (aromatic); 31.7 (alkyl). 19F-NMR: δ −118.5 ppm.

Workup

  1. temperaturewere refluxed under argon for 3 hours
  2. filtrationThe hot solution was filtered through a glass
  3. filtrationsintered filter
  4. washrinsed with 20 mL of hot CCl4, until the crystals
  5. washThe crystals were washed with 6 mL of cold CCl4
  6. concentrationthe solution was concentrated under reduced pressure
  7. customThe crude product was recrystallized from hexane
  8. customdried under vacuum

Sources & evidence

ORD record
ord-a15017cb81524c4f87d908ad932420c9
Source dataset
uspto-grants-2010_08
Patent number
US07776535B2

Reaction notes

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