Benzoyl Peroxide → HCID 18755534, compound

HRID 1838637Notes

Reaction equation

HRID 1838637 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 acetate/hexane 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 acetate/hexane 1:4)

Sources & evidence

ORD record
ord-f4043bf16a994b748a0754c91fbbc7ce
Source dataset
uspto-grants-2004_01
Patent number
US06673938B1

Reaction notes

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