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

HRID 471436
Notes
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Reaction equation

HRID 471436 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 11186
Zinc cyanide (Zn(CN)2)
Catalyst
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 152416121,1`-Bis(diphenylphosphino)ferroceneCatalyst

Conditions

Temperature
70 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-ed793eb191b6435b88dc95a997b4abab
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08633182B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes