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2-(4-Bromophenyl)ethanol → 2-{2-[4-(2-Hydroxy-ethyl)phenyl]-vinyl}-isoindole-1,3-dione

HRID 2383368
ノート
印刷プレビュー

反応式

HRID 2383368 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH:20]([N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32])=[CH2:21].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C>[OH:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH:21]=[CH:20][N:22]2[C:23](=[O:32])[C:24]3[C:25](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]2=[O:27])=[CH:3][CH:4]=1
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

6

反応物 4

HCID 728512-(4-Bromophenyl)ethanolHCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-HCID 80271Tri-o-tolylphosphineHCID 81531Diisopropylethylamine

生成物 1

HCID 670291452-{2-[4-(2-Hydroxy-ethyl)phenyl]-vinyl}-isoindole-1,3-dione

試薬・触媒・溶媒 1

HCID 6342Acetonitrile
溶媒

反応条件

温度
90 °C

実験手順

To a solution of 2-(4-bromophenyl)ethanol (48.3 g) in acetonitrile (480 mL) was added diisopropylethylamine (46.6 g), N-vinylphthalimide (43.7 g) and tri-o-tolylphosphine (7.31 g) and the mixture was purged with nitrogen gas three times. Palladium acetate (2.7 g) was added and the mixture was stirred at 90° C. for 21 hr under nitrogen. The reaction was cooled and the precipitated product collected by filtration. The resulting solid was re-dissolved in dichloromethane and ethyl acetate and filtered through silica gel. The filtrate was concentrated in vacuo to give the title compound, 24 g.

後処理

  1. customthe mixture was purged with nitrogen gas three times
  2. additionPalladium acetate (2.7 g) was added
  3. temperatureThe reaction was cooled
  4. filtrationthe precipitated product collected by filtration
  5. dissolutionThe resulting solid was re-dissolved in dichloromethane
  6. filtrationethyl acetate and filtered through silica gel
  7. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-18504441bd204a2089c41bc9ea38e454
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08263623B2

反応ノート

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