Hydrogen Bromide → 3-(2-Bromoacetyl)pyridine

HRID 450024Notes

Reaction equation

HRID 450024 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[BrH:10].[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(O)(=O)C>[Br:10][CH2:2][C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 95893-AcetylpyridineHCID 21124087Pyridiniumtribromide

Product 1

HCID 1514083-(2-Bromoacetyl)pyridineYield 52%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 3-acetyl pyridine (2.71 ml, 24.74 mmol) in acetic acid (7.5 ml) was added 33% hydrobromic acid in acetic acid (7.5 ml) and then pyridinium tribromide (8.70 g, 27.21 mmol). The reaction mixture was stirred at room temperature for 12 hr to give a solid. The solid was filtered, washed with acetic acid and hexane and then dried under vacuum to give 2-bromo-1-pyridin-3-yl-ethanone 3.61 g (52%).

Workup

  1. customto give a solid
  2. filtrationThe solid was filtered
  3. washwashed with acetic acid and hexane
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f95250e18be141abae601a65624c605c
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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