Bromine → 2-bromo-1-(6-bromopyridin-3-yl)ethanone

HRID 1187432Notes

Reaction equation

HRID 1187432 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[Br:11]Br>C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+].[Cl-].[Al+3].[Cl-].[Cl-]>[Br:11][CH2:9][C:8]([C:5]1[CH:6]=[N:7][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:10]

Participants

6

Reactant 2

HCID 24408BromineHCID 156681955-Acetyl-2-bromopyridine

Product 1

HCID 108502672-bromo-1-(6-bromopyridin-3-yl)ethanoneYield 110%

Reagents, catalysts & solvents 3

HCID 6451240Aluminum(III) ChlorideCatalystHCID 6212ChloroformSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1-(6-bromo-pyridin-3-yl)-ethanone (20.3 g, 101 mmol) and aluminum chloride (200 mg, 1.5 mmol) in chloroform (288 mL) was added bromine (5.23 mL, 101 mmol). The mixture was stirred at rt for 16 h. Upon completion of the reaction as judged by LC/MS analysis, the solution was diluted with sat aq NaHCO3 and extracted with DCM. The organic layer was removed, dried over MgSO4, filtered and concentrated giving rise to 31 g 2-bromo-1-(6-bromopyridin-3-yl)ethanone, which was taken on immediately. LC/MS: m/e 277.9 (M+H).

Workup

  1. customUpon completion of the reaction
  2. extractionextracted with DCM
  3. customThe organic layer was removed
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1d877aec02d04f359906a8f4a9add368
Source dataset
uspto-grants-2014_03
Patent number
US08673941B2

Reaction notes

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