Bromine → 4-(p-Fluorophenyl)-1-bromo-1-silacyclohexane
Reaction equation
[Br:1]Br.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][SiH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1>ClCCl>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:11][CH2:12][SiH:13]([Br:1])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Subsequently, 11.8 g of bromine was added to a solution of 14.0 g of 4-(p-fluorophenyl)-1-silacyclohexane in 100 ml of dichloromethane to obtain 4-(p-fluorophenyl)-1-bromo-1-silacyclohexane. The reaction solution was concentrated and the resultant residue was dissolved in 50 ml of diethyl ether, followed by dropping in 100 ml of a THF solution of 1 mole/liter of n-heptylmagnesium bromide at room temperature. The reaction mixture was poured into 200 ml of 5% hydrochloric acid and extracted with ethyl acetate. The resultant ethyl acetate solution was washed with brine, dried and concentrated, followed by purification through silica gel chromatography to obtain 19.0 g (yield: 90%) of the intended product. The results of IR and NMR analyses are shown below.
Sources & evidence
- ORD record
- ord-576a4967282844f58515bd0e0fb80371
- Source dataset
- uspto-grants-1996_06
- Patent number
- US05523439
Reaction notes
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