N-bromobutanimide → Ethanone, 1-[5-(bromomethyl)-6-chloro-2-pyridinyl]-

HRID 547273Notes

Reaction equation

HRID 547273 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[CH3:11].C1C(=O)N([Br:19])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:11][C:3]1[CH:4]=[CH:5][C:6]([C:8](=[O:10])[CH3:9])=[N:7][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 722140451-(6-Chloro-5-methylpyridin-2-YL)ethanone

Product 1

HCID 86011816Ethanone, 1-[5-(bromomethyl)-6-chloro-2-pyridinyl]-

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1-(6-chloro-5-methyl-pyridin-2-yl)-ethanone (1 eq) in CCl4 is added NBS (1 eq) and BPO (0.1 eq). The mixture is refluxed for 12 hours. After concentration, 1-(5-bromomethyl-6-chloro-pyridin-2-yl)-ethanone is isolated by flash column chromatography. MS: (ES+): 247.9 (M+1)+.

Workup

  1. temperatureThe mixture is refluxed for 12 hours
  2. concentrationAfter concentration

Sources & evidence

ORD record
ord-40b4b35627e54876a317bd41d345991f
Source dataset
uspto-grants-2011_05
Patent number
US07939519B2

Reaction notes

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