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Iodine → 1-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-2-(3-methoxy-phenyl)-ethanol

HRID 2101485
Notes
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Reaction equation

HRID 2101485 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Br.[Mg].II.[Cl:14][C:15]1[CH:16]=[C:17]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[CH2:18][N:19]1[CH:23]=[CH:22][N:21]=[C:20]1[CH:24]=[O:25]>C1COCC1.O>[Cl:14][C:15]1[CH:16]=[C:17]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[CH2:18][N:19]1[CH:23]=[CH:22][N:21]=[C:20]1[CH:24]([OH:25])[CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[C:3]([O:2][CH3:1])[CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 807IodineHCID 40672073-Methoxybenzyl bromide2×HCID 5462224MagnesiumHCID 578014901-(3,5-dichloro-benzyl)-1H-imidazole-2-carbaldehyde

Product 1

HCID 578015241-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-2-(3-methoxy-phenyl)-ethanolYield 304.8%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3-methoxy-benzylbromide (40 mg, 0.2 mmol), magnesium turnings (172 mg, 7.1 mmol) and a small crystal of iodine in dry THF (0.6 mL) was heated at 40° C. until an exothermic reaction to initiated. A solution containing a mixture of 1-(3,5-dichloro-benzyl)-1H-imidazole-2-carbaldehyde (255 mg, 1.0 mmol) and 3-methoxy-benzylbromide (241 mg, 1.2 mmol) in THF (2.5 mL) was then added dropwise to the stirred reaction mixture. After the addition was complete, the mixture was poured into cold water (20 mL) and extracted with CH2Cl2 (2×30 mL). The combined CH2Cl2 extracts were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 20:1 CH2Cl2/iPrOH) to provide the desired 1-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-2-(3-methoxy-phenyl)-ethanol (230 mg, 61%) as an off-white solid: ESI MS m/z 377 [C19H18Cl2N2O2+H]+.

Workup

  1. additionA solution containing
  2. additionwas then added dropwise to the stirred reaction mixture
  3. additionAfter the addition
  4. extractionextracted with CH2Cl2 (2×30 mL)
  5. dry with materialThe combined CH2Cl2 extracts were dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel, 20:1 CH2Cl2/iPrOH)

Sources & evidence

ORD record
ord-e7e0b55ff55f46df84d110faacd17ce8
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07572921B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes