Benzoyl Peroxide → HCID 67072139, compound

HRID 1242362Notes

Reaction equation

HRID 1242362 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:6][C:5]=1[CH3:20].[Br:22]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][CH:11]=2)=[N:6][C:5]=1[CH2:20][Br:22]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 670722692-Methyl-6-(4-trifluoromethyl-phenyl)-nicotinic Acid Methyl Ester

Product 1

HCID 67072139HCID 67072139, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
95 °C

Procedure

1.97 g (6.67 mmol) of 2-methyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester (example 1L]) was dissolved in 20 ml of CCl4 and treated with 1.781 g (10.0 mmol) of N-bromosuccinimide and 0.126 g (0.669 mmol) of dibenzoyl peroxide. The mixture was refluxed (oilbath temperature 95° C.) and the course of the bromination followed by GC. After 5 h, the reaction mixture was poured onto crashed ice, extracted twice with AcOEt, washed with water and brine, and dried over magnesium sulfate. Evaporation of the solvents i. V., followed by careful flash chromatography (SiO2, hexane/AcOEt=92/8), afforded 1.39 g of the title compound as white crystals, contaminated with roughly 5% of the dibromo-analogue.

Workup

  1. additionthe reaction mixture was poured
  2. extractionextracted twice with AcOEt
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvents i

Sources & evidence

ORD record
ord-981b36e0c4184c03b98d39c3764277e3
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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