Imidazole → 3-(t-Butyldimethylsiloxy)iodobenzene

HRID 2245859Notes

Reaction equation

HRID 2245859 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.[C:14]([Si:18]([CH3:21])([CH3:20])Cl)([CH3:17])([CH3:16])[CH3:15]>ClCCl>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][Si:18]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 122723-IodophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 27572803-(t-Butyldimethylsiloxy)iodobenzeneYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
15 °C

Procedure

3-Iodophenol (110 g, 0.50 mol, 1 eq) and imidazole (93.6 g, 1.375 mol, 2.75 eq) were placed in a 2000 ml flask with dichloromethane (1150 mL) and cooled in an ice water bath to 15° C. under nitrogen. tert-Butyldimethylchlorosilane (82.9 g, 0.55 mol, 1.1 eq) in dichloromethane (200 mL) was added dropwise through an addition funnel and the reaction mixture was stirred overnight. The reaction solution was washed with 0.5 N sodium hydroxide solution (3×200 mL), water (3×200 mL) and brine (200 ml) and dried over sodium sulfate. The solvent was removed under reduced pressure leaving 166.34 g of crude (3-iodo-phenoxy)-tert-butyl-dimethyl-silane. 1H NMR (300 MHz, CDCl3) δ 7.27 (ddd, J=8.0, 2.0, 1.0 Hz), 7.19 (dd, 1H, J=2.0, 2.0 Hz), 6.92 (dd, 1H, J=8.0, 8.0 Hz), 6.77 (ddd, 1H, J=8.0, 2.0, 1.0 Hz).

Workup

  1. washThe reaction solution was washed with 0.5 N sodium hydroxide solution (3×200 mL), water (3×200 mL) and brine (200 ml)
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1426a16e95e444b3b163bf7dd2dd1579
Source dataset
uspto-grants-2010_03
Patent number
US07683168B2

Reaction notes

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