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Water → 4-Bromo-1-oxo-indan-5-carbonitrile

HRID 471436
ノート
印刷プレビュー

反応式

HRID 471436 の反応式
[Br:1][C:2]1[C:10](OS(C(F)(F)F)(=O)=O)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:19].C(OCC)(=O)C.O.[CH3:27][N:28](C)C=O>[C-]#N.[Zn+2].[C-]#N.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:1][C:2]1[C:10]([C:27]#[N:28])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:19]
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

8

反応物 4

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 867007694-bromo-1-oxo-2,3-dihydro-1H-inden-5-yl trifluoromethanesulfonate

生成物 1

HCID 867007704-Bromo-1-oxo-indan-5-carbonitrile

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒
HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 152416121,1`-Bis(diphenylphosphino)ferrocene触媒

反応条件

温度
70 °C

実験手順

Trifluoro-methanesulfonic acid 4-bromo-1-oxo-indan-5-yl ester (10.30 g, 28.68 mmol) is stirred in 50 mL of dry N,N-dimethylformamide under argon atmosphere. Zinc cyanide (1.01 g, 8.60 mmol), 1,1-bis(diphenylphosphino) ferrocene (1.58 g, 2.86 mmol) and tris(dibenzylideneacetone)dipalladium(0) (1.32 g, 1.44 mmol) are added the reaction mixture is warmed at 70° C. for 1 h. The reaction mixture is partioned between ethyl acetate and water, the organic phase is washed with brine, washed with water, dried over sodium sulfate and concentrated under vacuum. The crude product obtained is purified by flash chromatography (cyclohexane/ethyl acetate 99/01→50/50) to give the title compound (Yield: 2.2 g).

後処理

  1. washthe organic phase is washed with brine
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe crude product obtained
  6. customis purified by flash chromatography (cyclohexane/ethyl acetate 99/01→50/50)

出典と根拠

ORDレコード
ord-ed793eb191b6435b88dc95a997b4abab
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08633182B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート