Imidazole → HCID 46183083, compound

HRID 1819922Notes

Reaction equation

HRID 1819922 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH3:9].N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>CN(C=O)C>[Si:15]([O:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH3:9])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 168964-Bromo-2-methylphenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 46183083HCID 46183083, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. mixture of 2-hydroxy-5-bromotoluene(48.63 g, 260 mmol), DMF (260 ml), imidazole (18.58 g, 273 mmol) is added t-butyldimethylsilyl chloride (41.15 g, 273 mol) in portions. After stirring for 30 m, the reaction is warmed to RT and stirred for 16 h. The reaction mixture is poured into ice/water (1.25 l) and extracted with Et2O. The organic layer is washed with water (2×100 ml), 1N NaOH (2×5 ml), water, brine, MgSO4 dried, concentrated, chromatographed (hex), and azeotroped with toluene to give the title compound as an oil (75.7 g, 97%)

Workup

  1. stirringstirred for 16 h
  2. extractionextracted with Et2O
  3. washThe organic layer is washed with water (2×100 ml), 1N NaOH (2×5 ml), water, brine, MgSO4
  4. customdried
  5. concentrationconcentrated
  6. customchromatographed (hex)
  7. customazeotroped with toluene

Sources & evidence

ORD record
ord-0803c95352f94ce6a3a49f4df4139ccb
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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