Benzoyl Peroxide → HCID 14074334, compound

HRID 1723033Notes

Reaction equation

HRID 1723033 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:27][C:28]1[C:33]([CH3:34])=[CH:32][N:31]=[C:30]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:29]=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:34][C:33]1[C:28]([CH3:27])=[N:29][C:30]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[N:31][CH:32]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 14074333HCID 14074333, compound

Product 1

HCID 14074334HCID 14074334, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

5.54 g (31.1 mmol) of N-bromosuccinimide (NBS) and 6 mg of dibenzoyl peroxide were added to a solution of 5.53 g (30 mmol) of 4,5-dimethyl-2-phenylpyrimidine in 110 ml of CCl4, and the mixture was warmed to the boiling point for 5 minutes with stirring and irradiation with a daylight lamp with increased short-wave content (type: Osram UltraVitalux, 300 W, GUR 53). The NBS had then been consumed and converted into specifically light succinimide. It was filtered off under suction at room temperature and washed with a little CCl4. The filtrate was evaporated in vacuo, the residue was dissolved in 100 ml of diisopropyl ether, the solution was clarified over kieselguhr, and the clear filtrate was again evaporated in vacuo. 7.70 g, 94.5% purity according to the 1H NMR spectrum, of 5-bromomethyl-4-methyl-2-phenylpyrimidine (=92% yield), melting point 65°-66° C., were obtained, analysis: C12H11BrN2 (MW 263.15) calc. C 54.77, H 4.21, Br 30.37, N 10.65; found C 53.5, H 3.9, Br 31.3, N 10.0%.

Workup

  1. temperaturethe mixture was warmed to the boiling point for 5 minutes
  2. customirradiation with a daylight lamp with increased short-wave content (type: Osram UltraVitalux, 300 W, GUR 53)
  3. customThe NBS had then been consumed
  4. filtrationIt was filtered off under suction at room temperature
  5. washwashed with a little CCl4
  6. customThe filtrate was evaporated in vacuo
  7. dissolutionthe residue was dissolved in 100 ml of diisopropyl ether
  8. customthe clear filtrate was again evaporated in vacuo

Sources & evidence

ORD record
ord-9da014c93bf34421a457dfb9c3c301f6
Source dataset
uspto-grants-1989_08
Patent number
US04859670

Reaction notes

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