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

HRID 471436
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HRID 471436 반응식
[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]
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참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

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

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ed793eb191b6435b88dc95a997b4abab
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08633182B2

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