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

HRID 1857651Notes

Reaction equation

HRID 1857651 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-ethyl-diphenyl-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 litres 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 crystallization is observed. After filtration and drying the precipitate 179.24 g of expected product is obtained. Rf: 0.53 (thin layer chromatography, support: silica, eluant Cyclohexane/AcOEt 95/5). Melting point: 56° C. NMR (CDCl3, 300 MHz)

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. customcrystallization
  7. filtrationAfter filtration
  8. dry with materialdrying the precipitate 179.24 g of expected product
  9. customis obtained

Sources & evidence

ORD record
ord-bf87202d840d446bb7fa350d42c5d2eb
Source dataset
uspto-grants-2000_11
Patent number
US06147119

Reaction notes

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