Ammonia → (2-(4-(5-Bromo-2-chlorobenzyl)phenyl)ethynyl)triisopropylsilane

HRID 502089

反応式

HRID 502089 の反応式
C([Mg]Cl)(C)C.I[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:9][CH:8]=1.C([Cu])#N.[Li+].[Cl-].[Br:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38]Br)[CH:32]=1.[Cl-].[NH4+].N>O1CCCC1.O>[Br:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH:32]=1)[CH2:38][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:9][CH:8]=1

参加物

10

反応物 7

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 433294Lithium Chloride2 回HCID 115582804-Bromo-2-(bromomethyl)-1-chlorobenzeneHCID 57809611((4-Iodophenyl)ethynyl)triisopropylsilaneHCID 178418546HCID 178418546、化合物2 回HCID 178418918HCID 178418918、化合物

生成物 1

HCID 16065644(2-(4-(5-Bromo-2-chlorobenzyl)phenyl)ethynyl)triisopropylsilane

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-25 °C

実験手順

Under argon 0.66 ml of a 2 M solution of isopropylmagnesium chloride in tetrahydrofuran are added dropwise to a solution of 0.50 g (4-iodo-phenylethynyl)-triisopropyl-silane in 2.2 ml dry tetrahydrofuran chilled to −25° C. The solution is stirred for 30 min at −25° C. and then combined with 0.26 ml of a 1 M solution of CuCN*2 LiCl in tetrahydrofuran (prepared by dissolving CuCN and LiCl in the ratio 1:2). Shortly afterwards, 0.35 g 4-bromo-2-bromomethyl-1-chlorbenzene are added and the reaction mixture is brought up to −5° C. in the cooling bath. After 6 h stirring at −5° C. the solution is heated to ambient temperature and stirred overnight. Then a mixture of saturated ammonium chloride solution and 25% ammonia solution (9:1) is added and the resulting mixture is added to water. The organic phase is separated off and the aqueous phase is extracted with ethyl acetate, the combined organic phases are dried over sodium sulfate, and the solvent is removed. The residue is purified through silica gel (cyclohexane).

後処理

  1. customprepared
  2. customis brought up to −5° C. in the cooling bath
  3. stirringAfter 6 h stirring at −5° C. the solution
  4. temperatureis heated to ambient temperature
  5. stirringstirred overnight
  6. additionis added
  7. customThe organic phase is separated off
  8. extractionthe aqueous phase is extracted with ethyl acetate
  9. dry with materialthe combined organic phases are dried over sodium sulfate
  10. customthe solvent is removed
  11. customThe residue is purified through silica gel (cyclohexane)

出典と根拠

ORDレコード
ord-721fa65378ed438bac668584e3190458
出典データセット
uspto-grants-2010_08
特許番号
US07772378B2

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