Bromine → 5-Bromoacetyl-3-pyridinecarboxylic acid methyl ester hydrobromide

HRID 2379820Notes

Reaction equation

HRID 2379820 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[C:11]([C:13](=[O:15])[CH3:14])[CH:12]=1)=[O:6]>O1CCOCC1>[BrH:1].[CH3:3][O:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[C:11]([C:13](=[O:15])[CH2:14][Br:1])[CH:12]=1)=[O:6]

Participants

4

Reactant 2

HCID 24408BromineHCID 596459Methyl 5-acetylpyridine-3-carboxylate

Product 1

HCID 884423645-Bromoacetyl-3-pyridinecarboxylic acid methyl ester hydrobromideYield 157.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Bromine (6.0 g) was added slowly to a solution of 5-acetyl-3-pyridinecarboxylic acid methyl ester (6.0 g) in dioxane (50 ml) at room temperature. The mixture was stirred at room temperature for 1 hour and then heated at 60°-70° C. for 5 hours. The resulting precipitate was collected by filtration to afford 5-bromoacetyl-3-pyridinecarboxylic acid methyl ester hydrobromide (10.0 g).

Workup

  1. temperatureheated at 60°-70° C. for 5 hours
  2. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-4a166fb01880464d82667aabe0a42c1a
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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