Triethylamine → 3-[[Dimethyl(1,1,2-trimethylpropyl)silyl]oxy]benzene bromide
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:16][Si:17](Cl)([CH3:24])[C:18]([CH:21]([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(Cl)Cl.CN(C)C1C=CN=CC=1.CCCCCC>[Br-:1].[CH3:16][Si:17]([CH3:24])([C:18]([CH3:20])([CH3:19])[CH:21]([CH3:23])[CH3:22])[O:8][C:4]1[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
To a stirred solution of 3-bromophenyl alcohol (5.0 g, 26.7 mmol) and triethylamine (3.25 g, 32.1 mmol) in anhydrous CH2Cl2 (125 mL) at room temperature under argon was added dropwise dimethylthexyl-silylchloride (5.26 g, 29.4 mmol). After 1.5 hours, 4-dimethylaminopyridine (0.50 g) was added and the stirring was continued for an additional 3 hours. The reaction mixture was diluted with hexane (200 mL) and the precipitate was filtered off. The filtrate was concentrated, partitioned between hexane (200 mL) and lN aqueous HCl (3×40 mL), and the organic layer was washed with saturated aqueous NaHCO3 (2×40 mL). The organic layer was dried (MgSO4), filtered and concentrated to yield title bromide (8.01 g, 91%).
Workup
- waitthe stirring was continued for an additional 3 hours
- filtrationthe precipitate was filtered off
- concentrationThe filtrate was concentrated
- custompartitioned between hexane (200 mL) and lN aqueous HCl (3×40 mL)
- washthe organic layer was washed with saturated aqueous NaHCO3 (2×40 mL)
- dry with materialThe organic layer was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6cdb1eb50ffe4ba6bbcf7c777f9dc7bc
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05100889
Reaction notes
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