Bromine → HCID 178433278, compound

HRID 280751Notes

Reaction equation

HRID 280751 reaction equation
[C:1]([C:4]1[NH:8][CH:7]=[N:6][C:5]=1[CH3:9])(=[O:3])[CH3:2].[Br:10]Br>Br>[CH3:9][C:5]1[N:6]=[CH:7][NH:8][C:4]=1[C:1](=[O:3])[CH2:2][Br:10]

Participants

4

Reactant 2

HCID 24408BromineHCID 178467483HCID 178467483, compound

Product 1

HCID 178433278HCID 178433278, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent2×

Procedure

A solution of 1.57 g (12.6 mmol) of 5-acetyl-4-methylimidazole in 15 ml of concentrated hydrobromic acid was warmed to 50° and a solution of 2.01 g (12.6 mmol) of bromine in 15 ml of concentrated hydrobromic acid was added over 0.75 hour. The mixture was stirred at 50° for 1.25 hour, then concentrated. The residue was triturated with isopropyl alcohol and the white solid was collected by filtration. This amounted to 2.78 g (78%) of 1-(4-methyl-5-imidazolyl)-2-bromoethanone hydrobromide: nmr (D6DMSO) (δ): 9.40 (s, 1H); 4.87 (s, 2H); 2.65 (s, 3H). This material was converted to its free base by stirring for 15 minutes in 50 ml of saturated sodium bicarbonate solution to give, after collection by filtration and drying, 1-(4-methyl-5-imidazolyl)-2-bromoethanone as a white powder.

Workup

  1. concentrationconcentrated
  2. customThe residue was triturated with isopropyl alcohol
  3. filtrationthe white solid was collected by filtration
  4. stirringby stirring for 15 minutes in 50 ml of saturated sodium bicarbonate solution
  5. customto give
  6. customafter collection
  7. filtrationby filtration
  8. customdrying

Sources & evidence

ORD record
ord-cbf860e3cb494ac8ae14c3fd4f529b22
Source dataset
uspto-grants-1986_05
Patent number
US04590299

Reaction notes

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