Chlorotrimethylsilane → (4-Ethylphenyl)(trimethyl)silane
Reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[CH:5][CH:4]=1.[CH3:11][Si:12](Cl)([CH3:14])[CH3:13].[NH4+].[Cl-]>C1COCC1>[CH2:9]([C:6]1[CH:7]=[CH:8][C:3]([Si:12]([CH3:14])([CH3:13])[CH3:11])=[CH:4][CH:5]=1)[CH3:10]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
Magnesium(9.5 g, 0.39 mole) was suspended in THF (60 mL) at room temperature. A solution of 4-bromo-1-ethylbenzene (49 mL, 0.36 mole) in 300 mL of THF was added dropwise at such a rate as to maintain the temperature between 30° and 60° C. When the addition was complete the reaction mixture was stirred for an additional hour and then cooled to 30° C. Trimethylsilyl chloride (49 mL, 0.39 mole) was added dropwise at such a rate as to maintain the temperature between 30° and 40° C. The thin suspension was stirred overnight at room temperature. Saturated aqueous NH4Cl was added and the reaction mixture partitioned. The aqueous phase was extracted three times with ether, and the combined organic phases were dried (MgSO4) and concentrated. The resultant oil (60 g, 93% yield) was used in the next step without further purification.
Workup
- temperatureto maintain the temperature between 30° and 60° C
- additionWhen the addition
- temperatureto maintain the temperature between 30° and 40° C
- stirringThe thin suspension was stirred overnight at room temperature
- customthe reaction mixture partitioned
- extractionThe aqueous phase was extracted three times with ether
- dry with materialthe combined organic phases were dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9aeb1ca2cefd4046b7d283a5ce4798e1
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05378708
Reaction notes
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