Bromine → HCID 178419746, compound

HRID 638219Notes

Reaction equation

HRID 638219 reaction equation
[OH:1][CH2:2][C:3]1[NH:4][CH:5]=[C:6]([C:8](=[O:10])[CH3:9])[N:7]=1.[Br:11]Br>Br>[BrH:11].[OH:1][CH2:2][C:3]1[NH:4][CH:5]=[C:6]([C:8](=[O:10])[CH2:9][Br:11])[N:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 178467224HCID 178467224, compound

Product 1

HCID 178419746HCID 178419746, compoundYield 112.8%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
80 °C

Procedure

1.826 g (0.013 mole) of 2-hydroxymethyl-4-acetylimidazole was dissolved in 40 ml of 48% hydrobromic acid and 2.1 g (0.013 mole) of bromine was added. The reaction was warmed at 80° C. for 2 hours and then concentrated in vacuo to a solid. This material was triturated with isopropyl ether and the resultant solid was collected by filtration and was washed with ether and dried to give 2.2 g (56%) of 2-hydroxymethyl-4-bromoacetylimidazole hydrobromide, m.p. 183° C. with decomposition. 1H-NMR(DMSO-d6)ppm(delta): 8.8 (s, 1H), 4.8 (s, 2×2H).

Workup

  1. concentrationconcentrated in vacuo to a solid
  2. customThis material was triturated with isopropyl ether
  3. filtrationthe resultant solid was collected by filtration
  4. washwas washed with ether
  5. customdried

Sources & evidence

ORD record
ord-121b7d65e5824aca8ef58275d925355a
Source dataset
uspto-grants-1985_12
Patent number
US04560690

Reaction notes

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