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

HRID 222565Notes

Reaction equation

HRID 222565 reaction equation
[Si:1](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Br:24][CH2:25][CH2:26][OH:27]>CCOCC.O>[Si:1]([O:27][CH2:26][CH2:25][Br:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 108982-BromoethanolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 10915442(2-Bromoethoxy)(tert-butyl)diphenylsilaneYield 101.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of tert-butyldiphenylsilyl chloride (20.32 g, 74.03 mmol) and imidazole (6.25 g, 91.9 mmol) was treated dropwise with 2-bromoethanol (47, 5 mL, 8.87 g, 70.8 mmol). Stirring was continued for 12 h. The mixture was diluted with Et2O and water. The phases were separated, and the aqueous layer was extracted Et2O. The organic extract was washed with water and dried over Na2SO4. Concentration of the sample yielded a pale brown oil (26.01 g, 97%): 1H NMR δ 1.11 (s, 9H), 3.45 (t, J=6.3 Hz, 2H), 3.96 (t, J=6.3 Hz, 2H), 7.42-7.47 (m, 6H), 7.70-7.73 (m, 4H); 13C NMR δ 19.52, 27.03, 33.43, 64.24, 128.04, 130.10, 133.49, 135.84.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted Et2O
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-c2f320f3e7f540439c86fa6a8d97a74d
Source dataset
uspto-grants-2012_06
Patent number
US08207329B2

Reaction notes

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