Imidazole → 4-Bromo-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-methoxybenzene
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH2:7][OH:8].N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH2:7][O:8][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]Participants
6
Procedure
To a solution of 2.17 g (10.0 mmol) of 5-bromo-2-methoxybenzyl alcohol in 10 mL of N,N-dimethylformamide was added 1.36 g (20.0 mmol) of imidazole, then 2.26 g (15.0 mmol) of tert-butyldimethylsilyl chloride. The reaction was stirred at ambient temperature for 30 min, and poured into 100 mL of water. The aqueous suspension was extracted with diethyl ether (3×15 mL), then the combined ether layers were back extracted with 1 M HCl (2×15 mL), saturated NaHCO3(aq.) (2×15 mL), and brine (1×15 mL), dried over MgSO4, filtered, and concentrated to an oil. This was purified via silica gel chromatography, eluting with 95:5 hexanes:ethyl acetate to give 2.91 g (88%) of the titled compound as a colorless oil.
Workup
- extractionThe aqueous suspension was extracted with diethyl ether (3×15 mL)
- extractionthe combined ether layers were back extracted with 1 M HCl (2×15 mL), saturated NaHCO3(aq.) (2×15 mL), and brine (1×15 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated to an oil
- customThis was purified via silica gel chromatography
- washeluting with 95:5 hexanes
Sources & evidence
- ORD record
- ord-a86e75e2e5614dffaf91f002561fa77b
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07888374B2
Reaction notes
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