2-Acetylpyridine → 3-(2-Bromoacetyl)pyridine hydrobromide

HRID 425438Notes

Reaction equation

HRID 425438 reaction equation
C([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)(=O)C.[BrH:10].[CH3:11][C:12]([OH:14])=O>>[BrH:10].[Br:10][CH2:11][C:12]([C:7]1[CH:6]=[N:5][CH:4]=[CH:9][CH:8]=1)=[O:14]

Participants

3

Reactant 2

HCID 142862-AcetylpyridineHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 27762343-(2-Bromoacetyl)pyridine hydrobromide

Conditions

Temperature
60 °C

Procedure

Acetylpyridine (120 g) is added to 33% HBr/AcOH (600 ml) with stirring (If the salt precipitates more AcOH, up to 800 ml may be added). Bromine (176 g) is added and the reaction mixture is heated to 60° C. for 2-3 h. The reaction mixture is cooled and ether (1400 ml) is added. The solid is filtered, washed with ether, and dried to give 2-bromo-1-(pyridin-3-yl)ethanone hydrobromide (Compound 13), in quantitative yield

Workup

  1. customprecipitates more AcOH
  2. additionup to 800 ml may be added)
  3. additionBromine (176 g) is added
  4. temperatureThe reaction mixture is cooled
  5. additionether (1400 ml) is added
  6. filtrationThe solid is filtered
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-b411456db6ca4a1f9266ee96063740e0
Source dataset
uspto-grants-2012_01
Patent number
US08106209B2

Reaction notes

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