Imidazole → HCID 18706297, compound

HRID 1797298Notes

Reaction equation

HRID 1797298 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].N1C=CN=C1.[CH:15]([Si:18](Cl)([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])([CH3:17])[CH3:16].O>C(Cl)Cl>[CH:15]([Si:18]([O:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[Br:1])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 728502-Bromobenzyl alcoholHCID 139400Triisopropylsilyl chloride

Product 1

HCID 18706297HCID 18706297, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of o-bromobenzyl alcohol (2.55 g, 13.6 mmol) and imidazole (1.36 g, 20 mmol) in CH2Cl2 (20 ml) was added triisopropylsilyl chloride (2.6 ml, 12 mmol) at RT. The obtained mixture was stirred at the same temperature for 1 h and then taken up to H2O. After phase separation, the aqueous phase was extracted twice with petroleum ether. The combined organic phases were dried over MgSO4 and concentrated in vacuo. The residue was purified by filtration through a short column of silica gel to give the title compound as a colorless liquid.

Workup

  1. customAfter phase separation
  2. extractionthe aqueous phase was extracted twice with petroleum ether
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. filtrationThe residue was purified by filtration through a short column of silica gel

Sources & evidence

ORD record
ord-7871bddd24484e04b89282e36fa5ee71
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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