Benzoyl Peroxide → HCID 68428407, compound

HRID 642403Notes

Reaction equation

HRID 642403 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([Cl:11])=[C:9]([Cl:12])[N:8]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:7]=1[CH3:18])=[O:5])[CH3:2].[Br:19]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([Cl:11])=[C:9]([Cl:12])[N:8]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:7]=1[CH2:18][Br:19])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 68427493HCID 68427493, compound

Product 1

HCID 68428407HCID 68428407, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4,5-Dichloro-2-methyl-1-(3-methyl-butyl)-1H-pyrrole-3-carboxylic acid ethyl ester (14.3 g, 48.9 mmol), N-bromosuccinimide (8.93 g, 50.2 mmol), and benzoyl peroxide (1.18 g, 4.89 mmol) were suspended in 123 mL of benzene and heated at reflux temperature for 16 hours. The reaction mixture was cooled and diluted with ethyl acetate. The reaction mixture was washed successively with saturated bicarbonate solution, brine, saturated ammonium chloride solution, and brine. The organic solvent was dried, filtered, and concentrated to afford 18.1 g of the crude 4,5-dichloro-2-bromomethyl-1-(3-methyl-butyl)-1H-pyrrole-3-carboxylic acid ethyl ester as a brown oil.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 16 hours
  3. temperatureThe reaction mixture was cooled
  4. washThe reaction mixture was washed successively with saturated bicarbonate solution, brine, saturated ammonium chloride solution, and brine
  5. customThe organic solvent was dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-93aa04db87064f34b11119c879e381f4
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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