Imidazole → [(3-Bromo-4-methoxybenzyl)oxy] (tert-butyl) dimethyl silane

HRID 1662749Notes

Reaction equation

HRID 1662749 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH3:12][C:13]([Si:16](Cl)([CH3:18])[CH3:17])([CH3:15])[CH3:14].N1C=CN=C1.O>CN(C=O)C.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][CH3:9])[CH2:10][O:11][Si:16]([C:13]([CH3:15])([CH3:14])[CH3:12])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 13551346(3-Bromo-4-methoxyphenyl)methanol

Product 1

HCID 86625718[(3-Bromo-4-methoxybenzyl)oxy] (tert-butyl) dimethyl silaneYield 100.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 98.8 g of the compound obtained in Step 204-1 in DMF (455 ml) was added 72.0 g of TBSCl and 62.0 g of imidazole under ice cooling, and the reaction mixture was stirred for 10 minutes. The solution was warmed to room temperature then stirred for two hours, water and Et2O were added and liquid separation was performed. The organic layer was washed with saturated brine and dried over MgSO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. n-hexane was used on the obtained solid residue for a recovery by filtration to obtain 152 g of the title compound.

Workup

  1. stirringthen stirred for two hours
  2. customliquid separation
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. customthe drying agent was separated by filtration
  6. customthe solvent was evaporated under reduced pressure
  7. filtrationn-hexane was used on the obtained solid residue for a recovery by filtration

Sources & evidence

ORD record
ord-4157bc0c1aa343cca3573b56b903fd06
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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