Bromine → HCID 178432761, compound

HRID 280755Notes

Reaction equation

HRID 280755 reaction equation
[C:1]([C:4]1[NH:8][C:7]([CH3:9])=[N:6][C:5]=1[CH3:10])(=[O:3])[CH3:2].[Br:11]Br>Br>[CH3:9][C:7]1[NH:8][C:4]([C:1](=[O:3])[CH2:2][Br:11])=[C:5]([CH3:10])[N:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 178467482HCID 178467482, compound

Product 1

HCID 178432761HCID 178432761, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 1.0 g (7.24 mmol) of 5-acetyl-2,4-dimethylimidazole in 15 ml of concentrated hydrobromic acid was warmed to 50° and 1.16 g (7.25 mmol) of bromine was added dropwise over 1 minute. The mixture was then heated at 50°-60° for 1 hour. The mixture was concentraed and the solid residue was triturated with 30 ml of saturated sodium bicarbonate solution. The insoluble material was collected by filtration, washed with water, and dried in vacuo to give 1.12 g (71%) of 1-(2,4-dimethyl-5-imidazolyl)-2bromoethanone as a white solid, mp 128°-132° . nmr (D6DMSO) (δ): 4.40 (s, 2H); 2.27 (s, 3H); 2.13 (s, 3H).

Workup

  1. temperatureThe mixture was then heated at 50°-60° for 1 hour
  2. customthe solid residue was triturated with 30 ml of saturated sodium bicarbonate solution
  3. filtrationThe insoluble material was collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e0ca10a8c7134a50bb532f4ba38df660
Source dataset
uspto-grants-1986_05
Patent number
US04590299

Reaction notes

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