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

HRID 1389485Notes

Reaction equation

HRID 1389485 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[CH3:14])=[CH:5][CH:4]=1.[BrH:15]>>[BrH:15].[CH3:14][C:10]1[N:9]([C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)[CH:13]=[CH:12][N:11]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 127971081-(4-methoxyphenyl)-2-methyl-1H-imidazole

Product 1

HCID 234610084-(2-methyl-1H-imidazol-1-yl)phenol monohydrobromideYield 69%

Procedure

A mixture of 4 parts of 1-(4-methoxyphenyl)-2-methyl-1H-imidazole and 37.5 parts of hydrobromic acid solution 48% is stirred and refluxed overnight. After cooling, the reaction mixture is evaporated. The residue is triturated in a mixture of 2-propanone and 2,2'-oxybispropane. The product is filtered off and crystallized from a mixture of ethanol and 2,2'-oxybispropane, yielding 3.8 parts (69%) of 4-(2-methyl-1H-imidazol-1-yl)phenol monohydrobromide; mp. 181°-205° C.

Workup

  1. temperaturerefluxed overnight
  2. temperatureAfter cooling
  3. customthe reaction mixture is evaporated
  4. customThe residue is triturated in a mixture of 2-propanone and 2,2'-oxybispropane
  5. filtrationThe product is filtered off
  6. customcrystallized from a mixture of ethanol and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-c3f5b316c58c4f57ab0f7738ebe67472
Source dataset
uspto-grants-1981_01
Patent number
US04244964

Reaction notes

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