Imidazole → (3-Bromophenoxy)tri(propan-2-yl)silane
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.[CH:14]([Si:17](Cl)([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])([CH3:16])[CH3:15]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][Si:17]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:14]([CH3:16])[CH3:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 3-bromophenol (1.00 g, 5.78 mmol), and imidazole (984 mg, 14.45 mmol) in 6 mL of DMF was cooled to 0° C. and triisopropylsilyl chloride (922 μL, 6.94 mmol) was added and the solution was stirred for 24 hours. The reaction mixture was quenched with 10 mL H2O and 5 mL saturated aqueous NaHCO3. The aqueous layer was extracted with ether (3×10 mL), the pooled organic extracts were washed with brine, dried (MgSO4), and concentrated. The resulting oil was flash chromatographed on silica gel with hexanes to yield 209 (1.50 g, 79%). 1H NMR (CDCl3) δ 1.09 (d, J=7.2 Hz, 18H), 1.17-1.30 (m, 3H), 6.75-6.81 (m, 1H), 7.00-7.10 (m, 3H); 13C NMR (CDCl3) 156.89, 130.26, 124.14, 123.29, 122.5, 118.47.
Workup
- customThe reaction mixture was quenched with 10 mL H2O and 5 mL saturated aqueous NaHCO3
- extractionThe aqueous layer was extracted with ether (3×10 mL)
- washthe pooled organic extracts were washed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customchromatographed on silica gel with hexanes
Sources & evidence
- ORD record
- ord-ece05c9c3cd24041b647cd3af3df9a1f
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07947726B2
Reaction notes
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