Imidazole → HCID 23499597, compound

HRID 1836549Notes

Reaction equation

HRID 1836549 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][C:10]=1[Br:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[C:23]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])([CH3:25])[CH3:24].O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][O:16][Si:27]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:29])[CH3:28])=[CH:11][C:10]=1[Br:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 17439222HCID 17439222, compound

Product 1

HCID 23499597HCID 23499597, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.0 g (10.23 mmol) of [4-(benzyloxy)-3-bromophenyl]methanol (Example I) are initially charged in 30 ml of DMF. At room temperature, 1.39 g (12.28 mmol) of 1H-imidazole (60% pure) and 2.01 g (13.3 mmol) of tert-butyl(chloro)dimethylsilane are added. The reaction mixture is stirred at room temperature overnight. Water is then added, and the mixture is extracted three times with diethyl ether. The combined organic phases are washed three times with water and once with saturated sodium chloride solution. The organic phase is dried with sodium sulphate and the solvent is removed under reduced pressure. This gives 4.02 g (86% of theory) of {[4-(benzyloxy)-3-bromobenzyl]oxy}(tert-butyl)dimethylsilane.

Workup

  1. extractionthe mixture is extracted three times with diethyl ether
  2. washThe combined organic phases are washed three times with water
  3. dry with materialThe organic phase is dried with sodium sulphate
  4. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-dbf5bce86c70495380ad6baab3b04383
Source dataset
uspto-grants-2004_08
Patent number
US06777442B2

Reaction notes

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