N-bromobutanimide → HCID 19867167, compound

HRID 1198838Notes

Reaction equation

HRID 1198838 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][Br:15])=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 11954577HCID 11954577, compound

Product 1

HCID 19867167HCID 19867167, compoundYield 110.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 0.248 g of 2-(p-bromophenyl)-5-methyl-pyridine, 0.196 g of N-bromosuccinimide, 20 mg of dibenzoyl peroxide and 5 ml of carbon tetrachloride was heated to reflux for 2.5 hours while gassing with nitrogen. The reaction mixture was subsequently left to cool to room temperature and suction filtered. The residue was rinsed with carbon tetrachloride. The filtrate was concentrated in a vacuum, there being obtained 0.360 g of crude 2-(p-bromophenyl)-5-bromomethyl-pyridine as brownish crystals.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2.5 hours
  3. waitThe reaction mixture was subsequently left
  4. filtrationsuction filtered
  5. washThe residue was rinsed with carbon tetrachloride
  6. concentrationThe filtrate was concentrated in a vacuum

Sources & evidence

ORD record
ord-1529500e3748459b924bd2334c9c71df
Source dataset
uspto-grants-1990_02
Patent number
US04898455

Reaction notes

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