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

HRID 412845

Reaction equation

HRID 412845 reaction equation
CN(C)C=O.N1C=CN=C1.[CH3:11][C:12]([Si:15]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)Cl)([CH3:14])[CH3:13].[Br:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1>C1CCCCC1.CCOC(C)=O.CCCCC.C(OCC)(=O)C.O>[Br:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][Si:15]([C:12]([CH3:14])([CH3:13])[CH3:11])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:32][CH:31]=1

Participants

9

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 78084-BromophenolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

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

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8003PentaneSolventHCID 8857Ethyl AcetateSolventHCID 21867204Cyclohexane ethylacetateSolvent

Procedure

400 ml of dimethylformamide, 31.18 g of imidazole and 125.89 g of 1,1-dimethyl-ethyldiphenyl-chlorosilane are added under an inert atmosphere and at ambient temperature to 80.89 g of parabromophenol, then the solution obtained is agitated for 2 hours. The reaction medium is poured into 2 liters of water, precipitation is observed, the solid is solubilized with ethyl acetate and the aqueous phase is extracted with ethyl acetate, the combined organic phases are dried and evaporated under reduced pressure until an oil is obtained. Pentane is added and crystallisation is observed. After filtration and drying of the precipitate 179.24 g of expected product is obtained. Rf: 0.53 (thin layer chromatography, support: silica, eluant Cyclohexane/AcOEt 95/5).

Workup

  1. customthe solution obtained
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. customthe combined organic phases are dried
  4. customevaporated under reduced pressure until an oil
  5. customis obtained
  6. customcrystallisation
  7. filtrationAfter filtration
  8. dry with materialdrying of the precipitate 179.24 g of expected product
  9. customis obtained

Sources & evidence

ORD record
ord-c58f3ff2753a4d5aad828e6b8423bd4a
Source dataset
uspto-grants-2003_05
Patent number
US06563008B2

Linked notes

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