Imidazole → HCID 69853166, compound

HRID 2175998Notes

Reaction equation

HRID 2175998 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.CN(C=O)C.[C:21]([Si:25](Cl)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:24])([CH3:23])[CH3:22]>O.C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][O:10][Si:25]([C:21]([CH3:24])([CH3:23])[CH3:22])([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 27340902-(3-Bromophenyl)ethan-1-ol

Product 1

HCID 69853166HCID 69853166, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 1.5 g of 2-(3-bromophenyl)ethanol, 1.0 g of imidazole and 15 mL of DMF was added 2.8 g of tert-butyl(chloro)diphenylsilane under ice cooling, and the followed by stirring for 1 hour at the same temperature then for a day at room temperature. Diethyl ether and water were added to the reaction mixture, followed by extraction with diethyl ether. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3), thereby obtaining 3.27 g of [2-(3-bromophenyl)ethoxy](tert-butyl)diphenylsilane.

Workup

  1. waitfor a day at room temperature
  2. extractionfollowed by extraction with diethyl ether
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-752fe81d2e9b451a944868d8fd285738
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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