Imidazole → (4-Bromo-2-ethylphenethoxy)(tert-butyl)dimethylsilane

HRID 735620Notes

Reaction equation

HRID 735620 reaction equation
N1C=CN=C1.[C:6]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:7].[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][OH:23])=[C:17]([CH2:24][CH3:25])[CH:16]=1>C(Cl)Cl>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][O:23][Si:10]([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:12])[CH3:11])=[C:17]([CH2:24][CH3:25])[CH:16]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 578427842-(4-Bromo-2-ethylphenyl)ethanol

Product 1

HCID 57842587(4-Bromo-2-ethylphenethoxy)(tert-butyl)dimethylsilaneYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Imidazole (2.1 g, 30.6 mmol) followed by tert-butylchlorodimethylsilane (2.5 g, 16.8 mmol) were added to a solution of 36B (3.5 g, 15.3 mmol) in CH2Cl2 (100 mL). The reaction mixture was stirred for 2 h then washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography (0% to 30% EtOAc in hexanes) to yield 46A (4.3 g, 82%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm −0.02 (s, 6 H) 0.86 (s, 9 H) 1.20 (t, J=7.42 Hz, 3 H) 2.63 (q, J=7.51 Hz, 2 H) 2.79 (t, J=7.15 Hz, 2 H) 3.74 (t, J=7.15 Hz, 2 H) 7.22 (dd, J=7.97, 1.92 Hz, 1 H) 7.29 (d, J=2.20 Hz, 1 H).

Workup

  1. washthen washed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography (0% to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d19aeb893e7049dbb2d7a3e214f70861
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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