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3,4-Dichlorobenzeneboronic acid → {[3-(3,4-Dichlorophenyl)-3-buten-1-yl]oxy}(1,1-dimethylethyl)diphenylsilane

HRID 639844
ノート
印刷プレビュー

反応式

HRID 639844 の反応式
Br[C:2](=[CH2:23])[CH2:3][CH2:4][O:5][Si:6]([C:19]([CH3:22])([CH3:21])[CH3:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][C:30]=1[Cl:31]>C1(C)C=CC=CC=1>[Cl:24][C:25]1[CH:26]=[C:27]([C:2](=[CH2:23])[CH2:3][CH2:4][O:5][Si:6]([C:19]([CH3:22])([CH3:21])[CH3:20])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:28]=[CH:29][C:30]=1[Cl:31]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 27343303,4-Dichlorobenzeneboronic acidHCID 11784074[(3-Bromo-3-buten-1-yl)oxy](1,1-dimethylethyl)diphenylsilane

生成物 1

HCID 59255999{[3-(3,4-Dichlorophenyl)-3-buten-1-yl]oxy}(1,1-dimethylethyl)diphenylsilane収率 64.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

[(3-Bromo-3-buten-1-yl)oxy](1,1-dimethylethyl)diphenylsilane (P12, 3.50 g) and (3,4-dichlorophenyl)boronic acid (2.06 g) were dissolved in toluene (45 mL), the stirred solution was degassed, then tetrakis(triphenylphosphine)palladium(0) (0.363 g) and ethanol (33 mL) were added and the mixture was degassed again. A 2N aqueous solution of Na2CO3 (24 mL) was added and the mixture was heated to 80° C. and stirred under nitrogen atmosphere for 3 h at this temperature. After cooling to RT, the reaction mixture was extracted with ethyl ether, the organic phase was washed with brine, dried over Na2SO4 and the solvent removed under reduced pressure. The crude product was purified by flash chromatography (eluting with cy/EA from 100/0 to 95/5) to give the title compound (2.65 g) as a colourless oil.

後処理

  1. customthe stirred solution was degassed
  2. additiontetrakis(triphenylphosphine)palladium(0) (0.363 g) and ethanol (33 mL) were added
  3. customthe mixture was degassed again
  4. additionA 2N aqueous solution of Na2CO3 (24 mL) was added
  5. temperatureAfter cooling to RT
  6. extractionthe reaction mixture was extracted with ethyl ether
  7. washthe organic phase was washed with brine
  8. dry with materialdried over Na2SO4
  9. customthe solvent removed under reduced pressure
  10. customThe crude product was purified by flash chromatography (eluting with cy/EA from 100/0 to 95/5)

出典と根拠

ORDレコード
ord-81ad3a8982524a26a0d7e925f1374c4d
出典データセット
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07691893B2

反応ノート

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