Benzoyl Peroxide → (3-Bromo-3-phenylpropoxy)(tert-butyl)dimethylsilane

HRID 451490ノート

反応式

HRID 451490 の反応式
[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:8][CH2:7][O:6][Si:5]([C:1]([CH3:3])([CH3:2])[CH3:4])([CH3:17])[CH3:16]

参加物

5

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 10083485Tert-butyldimethyl(3-phenylpropoxy)silane

生成物 1

HCID 67335370(3-Bromo-3-phenylpropoxy)(tert-butyl)dimethylsilane

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

A suspension of tert-butyldimethyl(3-phenylpropoxy)silane (2.22 g, 8.86 mmol), N-bromosuccinimide (1.58 g, 8.86 mmol) and benzoyl peroxide (66.4 mg, 266 μmol) in carbon tetrachloride (17.8 mL) was heated to reflux for 3 hours. The reaction was filtered, the precipitate washed with carbon tetrachloride and the solvent was evaporated. Water was added and the reaction was extracted twice with diethyl ether. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The title compound was obtained as a light yellow oil (1.63 g, 55%) after column chromatography on silica gel using heptane/ethyl acetate 19:1 (v/v) as eluent. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.42-7.26 (m, 5H), 5.42 (dd, 1H), 3.76 (m, 1H), 3.68 (m, 1H), 2.48 (m, 1H), 2.28 (m, 1H), 0.90 (s, 9H), 0.06 (s, 3H), 0.03 (s, 3H).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. filtrationThe reaction was filtered
  4. washthe precipitate washed with carbon tetrachloride
  5. customthe solvent was evaporated
  6. additionWater was added
  7. extractionthe reaction was extracted twice with diethyl ether
  8. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-adf8ea6fa3bf4ff4ad7f77e4ab8d39c9
出典データセット
uspto-grants-2013_07
特許番号
US08486967B2

反応ノート

読み込み中…