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

HRID 1780562Notes

Reaction equation

HRID 1780562 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>[C:6]([Si:10]([O:31][C:28]1[CH:29]=[CH:30][C:25]([Br:24])=[CH:26][CH:27]=1)([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]

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 stirring at room temperature for 1 hour, the reaction mixture is poured onto 1000 ml of 5% sodium bicarbonate solution, the resulting mixture is extracted twice with 400 ml of dichloromethane, the organic phase is washed with sodium chloride solution, dried over sodium sulfate, filtered and evaporated to dryness. Purification of the residue by chromatography (silica gel, 8:2 hexane/ethyl acetate) gives 23.40 g of 4-bromophenyl tert.-butyldiphenylsilyl ether. ##STR43##

Workup

  1. extractionthe resulting mixture is extracted twice with 400 ml of dichloromethane
  2. washthe organic phase is washed with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customPurification of the residue by chromatography (silica gel, 8:2 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-164530cdc87943afb031b3a39602231c
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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