Imidazole → (2-Bromoethoxy)(tert-butyl)diphenylsilane

HRID 1515656Notes

Reaction equation

HRID 1515656 reaction equation
[Br:1][CH2:2][CH2:3][OH:4].N1C=CN=C1.[C:10]([Si:14]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)Cl)([CH3:13])([CH3:12])[CH3:11]>ClCCl>[Br:1][CH2:2][CH2:3][O:4][Si:14]([C:10]([CH3:13])([CH3:12])[CH3:11])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 108982-BromoethanolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 10915442(2-Bromoethoxy)(tert-butyl)diphenylsilaneYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-bromoethanol (25 g, 200 mmol) and imidazole (41 g, 600 mmol) in dichloromethane (300 mL) was added tert-butyldiphenylchlorosilane (55 mL, 210 mmol) at room temperature and the mixture was stirred for 24 h. The resulting mixture was poured into ice-water, extracted with dichloromethane (2×250 mL), washed with brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, hexanes) afforded (2-bromo-ethoxy)-tert-butyl-diphenyl-silane (60 g, 83%) as a colorless oil.

Workup

  1. extractionextracted with dichloromethane (2×250 mL)
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, hexanes)

Sources & evidence

ORD record
ord-86bc6d7ac09b43b2b9cf86dbba07fad6
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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