p-Bromochlorobenzene → (4-chlorophenyl)[4-(1H-imidazol-1-yl)phenyl]methanol

HRID 543327

Reaction equation

HRID 543327 reaction equation
[Mg].[Cl:2][C:3]1[CH:8]=[CH:7][C:6](Br)=[CH:5][CH:4]=1.[N:10]1([C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=2)[CH:14]=[CH:13][N:12]=[CH:11]1.[Cl-].[NH4+]>CCOCC>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:19]([C:18]2[CH:17]=[CH:16][C:15]([N:10]3[CH:14]=[CH:13][N:12]=[CH:11]3)=[CH:22][CH:21]=2)[OH:20])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7806p-BromochlorobenzeneHCID 25517Ammonium ChlorideHCID 7365304-(1H-imidazol-1-yl)benzaldehydeHCID 5462224Magnesium

Product 1

HCID 3789353(4-chlorophenyl)[4-(1H-imidazol-1-yl)phenyl]methanolYield 83.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A Grignard reagent which is prepared by reacting 1.9 g of magnesium with 15 g of p-chlorobromobenzene in 40 ml of ether is added to a suspension of 6.2 g of 4-(1-imidazolyl)benzaldehyde in 70 ml of ether at 0° C. After the mixture is stirred at room temperature for an hour, the reaction mixture is poured into an aqueous ammonium chloride solution with caution. The mixture is extracted with chloroform and the chloroform is distilled off. The residue is purified column-chromatographically and recrystallized from toluene to give 8.6 g of α-(4-chlorophenyl)-4-(1-imidazolyl)benzenemethanol as white crystals, melting at 148.5°-149.5° C.

Workup

  1. extractionThe mixture is extracted with chloroform
  2. distillationthe chloroform is distilled off
  3. customThe residue is purified column-chromatographically
  4. customrecrystallized from toluene

Sources & evidence

ORD record
ord-fbef6326b9b4418c86e7e0b275e619cf
Source dataset
uspto-grants-1987_04
Patent number
US04661603

Linked notes

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