Methyl iodide → 1-[3-(4-Bromobenzyl)-5-chloro-2-phenyl-3H-imidazol-4-yl]ethanol

HRID 1019252Notes

Reaction equation

HRID 1019252 reaction equation
[Br:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11]([CH:12]=[O:13])=[C:10]([Cl:14])[N:9]=[C:8]2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.[Mg].[CH3:24]I.OS([O-])(=O)=O.[Na+]>C1COCC1.C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]([CH:12]([OH:13])[CH3:24])=[C:10]([Cl:14])[N:9]=[C:8]2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 516919Sodium BisulfateHCID 5462224MagnesiumHCID 109157723-(4-Bromobenzyl)-5-chloro-2-phenyl-3H-imidazole-4-carbaldehyde

Product 1

HCID 184001141-[3-(4-Bromobenzyl)-5-chloro-2-phenyl-3H-imidazol-4-yl]ethanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.8 g of 3-(4-bromobenzyl)-5-chloro-2-phenyl-3H-imidazole-4-carbaldehyde are dissolved in 50 ml of THF and a Grignard solution, prepared from 385 mg of magnesium turnings and 990 μl of methyl iodide in 50 ml of diethyl ether, is slowly added by syringe at RT. The mixture is stirred at RT for 3 days, then 200 ml of a 5% aqueous NaHSO4 solution are added und the mixture is extracted twice using 200 ml of EA each time. The extract is dried over Na2SO4 and the solvent is removed in vacuo. 3.7 g of a colorless oil are obtained.

Workup

  1. additionis slowly added by syringe at RT
  2. extractionis extracted twice
  3. dry with materialThe extract is dried over Na2SO4
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-16ad6f996315469893c3c80f577a692e
Source dataset
uspto-grants-2002_11
Patent number
US06486189B2

Reaction notes

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