Imidazole → tert-Butyl-(3,5-dibromobenzyloxy)diphenylsilane

HRID 2212319Notes

Reaction equation

HRID 2212319 reaction equation
N1C=CN=C1.[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([Br:15])[CH:14]=1)[CH2:10][OH:11].[Si:16](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([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>CN(C=O)C.C(OCC)(=O)C>[C:29]([Si:16]([O:11][CH2:10][C:9]1[CH:8]=[C:7]([Br:6])[CH:14]=[C:13]([Br:15])[CH:12]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([CH3:32])([CH3:30])[CH3:31]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 7009423(3,5-Dibromophenyl)methanol

Product 1

HCID 21964571tert-Butyl-(3,5-dibromobenzyloxy)diphenylsilaneYield 94.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

With stirring, imidazole (1.1 g, 16.0 mmol) is added to a solution of 3,5-dibromobenzyl alcohol (2.8 g, 10.5 mmol) in absolute DMF (20 ml), and the mixture is cooled to 0° C. tert-Butyldiphenylsilyl chloride (3.3 ml, 17.8 mmol) is added dropwise to the reaction solution, which is then stirred at 0° C. for 2 h. The mixture is then warmed to RT and stirred for another 2 h. The reaction mixture is diluted with ethyl acetate (20 ml) and extracted with a semisaturated aqueous NH4Cl solution (20 ml). The organic phase is dried over MgSO4, filtered off and concentrated under reduced pressure. Further purification is carried out by chromatography [PE/EA (99:1)] on a silica gel column. This gives the title compound (5.0 g) as a colorless solid. TLC, silica gel (glass plates), [petroleum ether/ethyl acetate (99:1)], Rf=0.8.

Workup

  1. additionis added dropwise to the reaction solution, which
  2. stirringis then stirred at 0° C. for 2 h
  3. stirringstirred for another 2 h
  4. extractionextracted with a semisaturated aqueous NH4Cl solution (20 ml)
  5. dry with materialThe organic phase is dried over MgSO4
  6. filtrationfiltered off
  7. concentrationconcentrated under reduced pressure
  8. customFurther purification

Sources & evidence

ORD record
ord-b61e584ea3d64e6aaebcf1e04f10c912
Source dataset
uspto-grants-2006_09
Patent number
US07101911B2

Reaction notes

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