Imidazole → (3-Bromophenoxy)(tert-butyl)dimethylsilane

HRID 1900258Notes

Reaction equation

HRID 1900258 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9]([Si:13](Cl)([CH3:15])[CH3:14])([CH3:12])([CH3:11])[CH3:10].N1C=CN=C1>CN(C)C=O>[Si:13]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 115633-BromophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11254705(3-Bromophenoxy)(tert-butyl)dimethylsilaneYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1400 g (8.1 mol) of 3-bromophenol, 1218 g (8.1 mol) of tert-butylchlorodimethylsilane and 1376 g (20.2 mol) of imidazole in 1600 mL of N,N-dimethylformamide was stirred at room temperature under nitrogen for 18 hours. The reaction mixture was poured into pH 8 aqueous buffer solution and extracted with diethyl ether. The ether extracts were washed with water and brine, dried over sodium sulfate, and the solvent was evaporated under vacuum to give 2314 g of crude 3-bromophenyl tert-butyldimethylsilyl ether as an orange oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ether extracts were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-c8477a91abb54d7abb85668d71282b34
Source dataset
uspto-grants-1996_11
Patent number
US05574159

Reaction notes

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