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

HRID 471436Notes

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]

Participants

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

washthe organic phase is washed with brine
washwashed with water
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum
customThe crude product obtained
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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