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 dimethylthexylsilylchloride (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 1N 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 1N 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-2120ce38006b45ea849d9d008495a88d
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05153327
Linked notes
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