Benzoyl Peroxide → HCID 18755534, compound

HRID 1861604Notes

Reaction equation

HRID 1861604 reaction equation
[Cl:1][C:2]1[C:7]([CH3:9])([CH3:8])[C:6](=[O:10])[C:5]([CH3:12])([CH3:11])[C:4](=[O:13])[C:3]=1[C:14]([C:16]1[C:17]([CH3:26])=[N:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=1)=[O:15].[Br:27]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:27][CH2:26][C:17]1[C:16]([C:14]([C:3]2[C:4](=[O:13])[C:5]([CH3:12])([CH3:11])[C:6](=[O:10])[C:7]([CH3:9])([CH3:8])[C:2]=2[Cl:1])=[O:15])=[CH:21][CH:20]=[C:19]([C:22]([F:23])([F:24])[F:25])[N:18]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 11383649HCID 11383649, compound

Product 1

HCID 18755534HCID 18755534, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

0.39 g (1 mmol) of 5-chloro-2,2,6,6-tetramethyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-4-ene-1,3-dione and 0.20 g (1.1 mmol) of N-bromsuccinimide are refluxed in the presence of a catalytic amount of dibenzoyl peroxide in 10 ml of carbon tetrachloride. After the reaction has subsided, the resulting succinimide is removed by filtration and the crude product is purified by column chromatography (mobile phase: ethyl acetatelhexane 1:4). This gives pure 4-(2-bromomethyl-6-trifluoromethylpyridine-3-carbonyl)-5-chloro-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione of melting point 94.5-95° C.

Workup

  1. customthe resulting succinimide is removed by filtration
  2. customthe crude product is purified by column chromatography (mobile phase: ethyl acetatelhexane 1:4)

Sources & evidence

ORD record
ord-47fb2b8533d4474b9ac38ef75ccb57df
Source dataset
uspto-grants-2003_03
Patent number
US06534445B1

Reaction notes

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