Dichloromethane → 2-[2-[[Dimethyl(1,1,2-trimethylpropyl)silyl]oxy]ethyl]benzene bromide
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6][OH:7].CN(C1C=[CH:18][CH:17]=[CH:16]N=1)C.C(N([CH2:25][CH3:26])CC)C.[CH3:27][Si:28](Cl)(C)[CH2:29]CCCCC.[CH2:37](Cl)Cl>CCCCCC>[Br-:1].[CH3:27][Si:28]([CH3:29])([C:25]([CH3:26])([CH3:37])[CH:17]([CH3:18])[CH3:16])[O:7][CH2:6][CH2:5][C:4]1[CH:3]=[CH:2][CH:10]=[CH:9][CH:8]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3-Bromophenethyl alcohol (46.0 g, 228.78 mmol) was combined with dimethylaminopyridine (6.99 g, 57.19 mmol) and triethylamine (34.73 g, 343.17 mmol) in anhydrous CH2Cl2 (200 mL) and cooled to 0° C. Dimethylhexylsilyl chloride (44.18 g, 247.08 mmol) was added dropwise over ten minutes, then the reaction mixture was warmed to room temperature and stirred for sixteen hours. The reaction mixture was diluted with hexane (800 mL) and filtered. The filtrate was concentrated and the residue was partitioned between ether (800 mL) and 0.3N aqueous HCl (2 times with 400 mL), saturated aqueous NaHCO3 (400 mL), dried (MgSO4) and concentrated. The crude liquid was chromatographed on a silica gel column and eluted with 20% ether in hexane to give title compound (74.45 g, 95%) as a clear liquid.
Workup
- temperaturethe reaction mixture was warmed to room temperature
- filtrationfiltered
- concentrationThe filtrate was concentrated
- customthe residue was partitioned between ether (800 mL) and 0.3N aqueous HCl (2 times with 400 mL), saturated aqueous NaHCO3 (400 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe crude liquid was chromatographed on a silica gel column
- washeluted with 20% ether in hexane
Sources & evidence
- ORD record
- ord-95a1f4b546d442b1b6f8ed00c139391d
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05153327
Reaction notes
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