Bromine → HCID 178432761, compound

HRID 1980594Notes

Reaction equation

HRID 1980594 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 concentrated 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)-2-bromoethanone 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. concentrationThe mixture was concentrated
  3. customthe solid residue was triturated with 30 ml of saturated sodium bicarbonate solution
  4. filtrationThe insoluble material was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-6510cad5f0a84920b4de828f3dd1ed01
Source dataset
uspto-grants-1985_04
Patent number
US04510313

Reaction notes

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