Hydrogen Bromide → 4-(1-ethyl-1H-imidazol-2-yl)phenol

HRID 484667Notes

Reaction equation

HRID 484667 reaction equation
Cl.[CH2:2]([N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=1)[CH3:3].Br>C(O)(=O)C>[CH2:2]([N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[CH3:3]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 202717111-ethyl-2-(4-methoxyphenyl)-1H-imidazole monohydrochloride

Product 1

HCID 1358155694-(1-ethyl-1H-imidazol-2-yl)phenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 7 parts of 1-ethyl-2-(4-methoxyphenyl)-1H-imidazole monohydrochloride and 75 parts of hydrobromic acid solution 48% in glacial acetic acid is stirred and a refluxed for 2 hours. The reaction mixture is concentrated and a small amount of water is added to the concentrate. The whole is neutralized with sodium hydrogen carbonate. The precipitated product is filtered off and crystallized from a mixture of ethanol and water, yielding 3.3 parts of 4-(1-ethyl-1H-imidazol-2-yl)phenol.

Workup

  1. temperaturea refluxed for 2 hours
  2. concentrationThe reaction mixture is concentrated
  3. additiona small amount of water is added to the concentrate
  4. filtrationThe precipitated product is filtered off
  5. customcrystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-1384605fa118448aa3eeade454131964
Source dataset
uspto-grants-1985_08
Patent number
US04533550

Reaction notes

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