Iodine → Allyl(chloromethyl)[bis(4-fluorophenyl)]silane
Reaction equation
[Mg].II.Br[CH2:5][CH:6]=[CH2:7].[F:8][C:9]1[CH:14]=[CH:13][C:12]([Si:15]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)(Cl)[CH2:16][Cl:17])=[CH:11][CH:10]=1.[Cl-].[NH4+]>CCOCC>[CH2:5]([Si:15]([CH2:16][Cl:17])([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:12]1[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=1)[CH:6]=[CH2:7]Participants
Procedure
A mixture of 1.04 g (0.0428 mol) of magnesium turnings and about 0.05 g of iodine in 50 ml of ether was stirred under nitrogen while a solution of 4.7 ml (0.0544 mol) of 3-bromopropene in ether was added dropwise. The iodine color quickly disappeared, and the reaction temperature was kept around 30° C. by cooling with ice-water. The resulting solution was stirred 2 hours at room temperature. A solution of 10.0 gm (0.033 mol) of bis(4-fluorophenyl)chlorochloromethylsilane in 20 ml of ether was then added over 5 minutes, and the resulting mixture was allowed to stir overnight. The solution was treated with 20 ml of saturated aqueous ammonium chloride and extracted with ether. The ether was washed with water and with brine. Drying over magnesium sulfate and removal of solvent afforded a clear colorless oil which was distilled at 0.4 torr (bp 120°-130° C.) to give the title compound: nmr (CDCl3) 2.3 (2H, d, J=8 Hz), 3.3 (1H, s), 5.0 (2H, m), 5.8 (1H, m), 7.1 (4H, t, J=9 Hz), 7.6 (4H, d of d, J=9,6 Hz).
Workup
- additionwas added dropwise
- customwas kept around 30° C.
- stirringto stir overnight
- extractionextracted with ether
- washThe ether was washed with water and with brine
- dry with materialDrying over magnesium sulfate and removal of solvent
- customafforded a clear colorless oil which
- distillationwas distilled at 0.4 torr (bp 120°-130° C.)
Sources & evidence
- ORD record
- ord-d4debc089f1b48cb9779ca6c4e512cde
- Source dataset
- uspto-grants-1985_07
- Patent number
- US04530922
Reaction notes
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