Imidazole → Silane, (4-bromophenoxy)(1,1-dimethylethyl)diphenyl-

HRID 1780069Notes

Reaction equation

HRID 1780069 reaction equation
N1C=CN=C1.[C:6]([Si:10](Cl)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:9])([CH3:8])[CH3:7].[Br:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Si:10]([O:31][C:28]1[CH:29]=[CH:30][C:25]([Br:24])=[CH:26][CH:27]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 78084-BromophenolHCID 94078tert-ButyldiphenylchlorosilaneHCID 516892Sodium Bicarbonate

Product 1

HCID 11292808Silane, (4-bromophenoxy)(1,1-dimethylethyl)diphenyl-Yield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

11.06 g (162.5 mmol) of imidazole in 30 ml of dimethylformamide are added dropwise at room temperature to 35.24 g (130.0 mmol) of tert-butylchlorodiphenylsilane and 11.25 g (65.0 mmol) of 4-bromophenol in 150 ml of dimethylformamide. After the reaction mixture has been stirred at room temperature for 1 hour, it is poured into 1000 ml of 5% strength aqueous sodium bicarbonate solution and extracted twice with 400 ml of dichloromethane, the organic phase is washed with aqueous sodium chloride solution, dried over sodium sulfate and filtered, and the filtrate is evaporated to dryness. Chromatographic purification (silica gel/hexane: ethyl acetate 8:2) gives 23.40 g of 4-bromophenyl tert-butyldiphenylsilyl ether. ##STR27##

Workup

  1. extractionextracted twice with 400 ml of dichloromethane
  2. washthe organic phase is washed with aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe filtrate is evaporated to dryness
  6. customChromatographic purification (silica gel/hexane: ethyl acetate 8:2)

Sources & evidence

ORD record
ord-d7ec37ff656a4eef9ac5909eec9e7c63
Source dataset
uspto-grants-1997_05
Patent number
US05629428

Reaction notes

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