4-Acetylpyridine → 4-(Bromoacetyl)pyridine hydrobromide

HRID 1435946Notes

Reaction equation

HRID 1435946 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br:10]Br>C(O)(=O)C.Br>[BrH:10].[Br:10][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 2

HCID 142824-AcetylpyridineHCID 24408Bromine

Product 1

HCID 27762394-(Bromoacetyl)pyridine hydrobromideYield 175.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 260Hydrogen BromideSolvent

Procedure

To a stirred solution of 4-acetylpyridine (10 mL, 90 mmol) in glacial acetic acid (40 mL) and 48% hydrobromic acid (15 mL), bromine (4.65 mL, 90 mmol) in glacial acetic acid (10 mL) was added dropwise. After addition, the solution was stirred at room temperature overnight. The white precipitate was filtered off and washed with absolute ethanol, thus obtaining the title compound (22.2 g, 90%) as a white solid containing traces of dibromoderivative, that was used as such in the next step.

Workup

  1. additionAfter addition
  2. filtrationThe white precipitate was filtered off
  3. washwashed with absolute ethanol

Sources & evidence

ORD record
ord-96801f7ed0cc40a2a55e8a4e90f9ae2a
Source dataset
uspto-grants-2009_11
Patent number
US07618982B2

Reaction notes

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