Iodine → Allyl(chloromethyl)[bis(4-fluorophenyl)]silane

HRID 371310ノート

反応式

HRID 371310 の反応式
[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]

参加物

7

反応物 5

HCID 807Iodine2 回HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 13392398Chloro(chloromethyl)[bis(4-fluorophenyl)]silane

生成物 1

HCID 13489944Allyl(chloromethyl)[bis(4-fluorophenyl)]silane

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒3 回

実験手順

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).

後処理

  1. additionwas added dropwise
  2. customwas kept around 30° C.
  3. stirringto stir overnight
  4. extractionextracted with ether
  5. washThe ether was washed with water and with brine
  6. dry with materialDrying over magnesium sulfate and removal of solvent
  7. customafforded a clear colorless oil which
  8. distillationwas distilled at 0.4 torr (bp 120°-130° C.)

出典と根拠

ORDレコード
ord-d4debc089f1b48cb9779ca6c4e512cde
出典データセット
uspto-grants-1985_07
特許番号
US04530922

反応ノート

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