Imidazole → [(3-Bromophenyl)methoxy](tert-butyl)diphenylsilane

HRID 1460092Notes

Reaction equation

HRID 1460092 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[C:10]([Si:14](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:13])([CH3:12])[CH3:11].N1C=CN=C1.CN(C)C=O>O>[Si:14]([O:6][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([Br:1])[CH:3]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 851413-Bromobenzyl alcoholHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 14903623[(3-Bromophenyl)methoxy](tert-butyl)diphenylsilaneYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-bromobenzyl alcohol (15.0 g, 80 mmol), tert-butylchlorodiphenylsilane (22.9 mL, 88 mmol), imidazole (12.0 g, 176 mmol) and 75 mL of dimethylformamide was stirred at room temperature overnight. The reaction mixture was poured into cold water, extracted with diethyl ether, the extracts washed with water and brine, dried over sodium sulfate and evaporated. The resulting oil was purified by chromatography on silica gel with hexane to give 23.7 g (70%) of 3-bromobenzyl tert-butyldiphenylsilyl ether as a colorless oil.

Workup

  1. extractionextracted with diethyl ether
  2. washthe extracts washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe resulting oil was purified by chromatography on silica gel with hexane

Sources & evidence

ORD record
ord-421310bd94cc4984b103e4ae11b130b6
Source dataset
uspto-grants-1998_12
Patent number
US05854249

Reaction notes

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