Imidazole → [1,1'-Biphenyl]-4-methanol, a-(4-fluorophenyl)-a

HRID 1155282Notes

Reaction equation

HRID 1155282 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C[O-].[Na+].[C:9]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:14]=[CH:13][C:12]([C:15]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)([OH:18])[CH2:16]Cl)=[CH:11][CH:10]=1.CN(C)C=O>CO>[C:9]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:14]=[CH:13][C:12]([C:15]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)([OH:18])[CH2:16][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 13013625HCID 13013625, compound

Product 1

HCID 13013626[1,1'-Biphenyl]-4-methanol, a-(4-fluorophenyl)-aYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

20.2 g (0.297 mol) of imidazole are added to a solution of 9.5 g (0.175 mol) of sodium methylate in 49 ml of methyl alcohol. A slution of 44.3 g (0.135 mol) of 1-(4-biphenylyl)-2-chloro-1-(4-fluorophenyl)-ethanol in 103 mol of dimethylformamide is then added dropwise, and the reaction mixture is heated to 60° C. for 90 minutes. It is concentrated by distilling off the solvent in vacuo, and the residue is stirred with water. The crystals which remain are washed with acetonitrile and recrystallised from ethyl alcohol. 13.5 g (28% of theory) of 1-(4-biphenylyl)-1-(4-fluorophenyl)-2-(imidazol-1-yl)-ethanol of melting point 220° C. are obtained.

Workup

  1. concentrationIt is concentrated
  2. distillationby distilling off the solvent in vacuo
  3. washThe crystals which remain are washed with acetonitrile
  4. customrecrystallised from ethyl alcohol

Sources & evidence

ORD record
ord-0b4288c5cab14abfa99c3900afbbb84e
Source dataset
uspto-grants-1981_11
Patent number
US04301166

Reaction notes

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