Benzoyl Peroxide → 4-(4-Fluorobenzoyl)benzyl bromide

HRID 502492Notes

Reaction equation

HRID 502492 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[O:7])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 47290124-Fluoro-4'-methylbenzophenone

Product 1

HCID 47290134-(4-Fluorobenzoyl)benzyl bromideYield 43%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2.0 g (9.9 mmol) of 4-methyl-4′-fluorobenzophenone, 1.524 g (9.9 mmol) of recrystallized N-bromosuccinimide, 170 mg benzoyl peroxide, and 20 mL CCl4 was 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 vacuum. The crude product was recrystallized from hexane and dried under vacuum. The resultant yield was 43%. Rf=0.25 (ethyl Acetate/hexane; 15:85). 1H-NMR: δ 7.85 (dd, aromatic, 2H), 7.75 (d, aromatic, 2H), 7.51 (d, aromatic, 2H), 7.17 (dd, aromatic, 2H), 4.52 (s, methyl, 3H). 13C-NMR: δ 195.0 (carbonyl); 166.5, 164.5, 142.5, 138.5, 133.4, 130.4, 129.2, 115.8, 115.5 (aromatic); 31.1 (alkyl).

Workup

  1. temperaturewas 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 vacuum
  7. customThe crude product was recrystallized from hexane
  8. customdried under vacuum

Sources & evidence

ORD record
ord-813a4953ca5c4c8f8a6692c3daba7a16
Source dataset
uspto-grants-2010_08
Patent number
US07776535B2

Reaction notes

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