Hydrogen Bromide → alpha-Bromo-3-methoxy-4-acetylpyridine hydrobromide

HRID 4358Notes

Reaction equation

HRID 4358 reaction equation
[BrH:1].[NH+]1C=CC=CC=1.Br.[CH3:9][O:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[C:17](=[O:19])[CH3:18]>C(O)(=O)C>[BrH:1].[Br:1][CH2:18][C:17]([C:16]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[O:10][CH3:9])=[O:19]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 128039871-(3-Methoxypyridin-4-yl)ethan-1-oneHCID 21226041Pyridinium hydrobromide

Product 1

HCID 86741822alpha-Bromo-3-methoxy-4-acetylpyridine hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

A solution of pyridinium hydrobromide perbromide (2.33 g, 0.0073 mol) in acetic acid (20 mL) containing 31% hydrobromic acid in acetic acid (1.85 mL) was stirred at room temperature for four hours. The mixture was cooled to 17° C. and a solution of 3-methoxy-4-acetylpyridine (1.02 g, 0.0062 mol) in acetic acid (5 mL) was added. The cooling bath was removed and after about thirty minutes a yellow solid was deposited. Ether (25 mL) was added and the crude α-bromo-3-methoxy-4-acetylpyridine hydrobromide (1.60 g) was collected by filtration washed with ether and air dried.

Workup

  1. temperatureThe mixture was cooled to 17° C.
  2. customThe cooling bath was removed and after about thirty minutes a yellow solid
  3. additionEther (25 mL) was added
  4. filtrationthe crude α-bromo-3-methoxy-4-acetylpyridine hydrobromide (1.60 g) was collected by filtration
  5. washwashed with ether and air
  6. customdried

Sources & evidence

ORD record
ord-2cbd4d49833e4296861b4aa4a8ba079b
Source dataset
uspto-grants-1988_02
Patent number
US04725606

Reaction notes

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