Benzoyl Peroxide → HCID 58969780, compound

HRID 502490Notes

Reaction equation

HRID 502490 reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=2[F:15])=[O:7])=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[C:9]([F:15])=[CH:10][CH:11]=[CH:12][C:13]=2[F:14])=[O:7])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27823144'-Methyl-2,6-difluorobenzophnone

Product 1

HCID 58969780HCID 58969780, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 233 mg (1 mmol) of 4-methyl-2′,6′-difluorobenzophenone, 178 mg (1 mmol) of recrystallized N-bromosuccinimide, 17 mg benzoyl peroxide, and 3 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 vacuum. The crude product was purified by column chromatography on a silica gel flash column (13 cm×55 mm) eluted with ethyl acetate/hexane (15:85) and then concentrated under vacuum. The product was allowed to dry under high vacuum overnight. The resultant yield was 55%. Rf=0.3 (ethyl Acetate/hexane; 15:85). 1H-NMR: δ 7.84 (d, 2H, aromatic), 7.50 (d, 2H, aromatic), 7.46 (t, 1H, aromatic), 7.01 (m, 2H, aromatic), 4.51 (s, 2H). 13C-NMR (CDCl3): δ 188.1 (carbonyl); 160.8, 158.8, 143.9, 136.6, 132.0, 130.0, 129.4, 111.9 (aromatic), 31.8 (alkyl bromide).

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 vacuum
  7. customThe crude product was purified by column chromatography on a silica gel flash column (13 cm×55 mm)
  8. washeluted with ethyl acetate/hexane (15:85)
  9. concentrationconcentrated under vacuum
  10. customto dry under high vacuum overnight

Sources & evidence

ORD record
ord-41e46e6e6d8648f198f6f4f1c4238555
Source dataset
uspto-grants-2010_08
Patent number
US07776535B2

Reaction notes

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