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Dichloromethane → 4-bromo-1-(4-methoxybenzyl)-1H-imidazole

HRID 868909
Notes
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Reaction equation

HRID 868909 reaction equation
[Br:1][C:2]1[NH:6][CH:5]=[N:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.ClCCl>CN(C=O)C>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:4]2[CH:3]=[C:2]([Br:1])[N:6]=[CH:5]2)=[CH:16][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 961251H-Imidazole, 4-bromo-

Product 1

HCID 461855504-bromo-1-(4-methoxybenzyl)-1H-imidazoleYield 67.2%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a suspension of 5-bromo-1H-imidazole (10 g, 68.5 mmol) and K2CO3 (37.8 g, 274 mmol) in DMF (100 mL) was added 1-(chloromethyl)-4-methoxybenzene (11.8 g, 75.4 mmol) dropwise at room temperature. The resulting mixture was stirred for 16 hours, and then dichloromethane (DCM) was added. The mixture was successively washed with water and brine, dried and concentrated to give a residue that was purified by column chromatography to afford 12.3 g of the desired compound as a solid. LC-MS: m/z 267 (M+H+).

Workup

  1. washThe mixture was successively washed with water and brine
  2. customdried
  3. concentrationconcentrated
  4. customto give a residue that
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-d07cceb076964d2a9dc13c23ab2832b1
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08969349B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes