2-Bromobenzonitrile → 2-(1-Oxo-indan-5-yl)-benzonitrile

HRID 1742403Notes

Reaction equation

HRID 1742403 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[CH2:10][CH2:9]2)CCC.Br[C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[C:27]#[N:28]>O1CCOCC1>[O:15]=[C:11]1[C:12]2[C:8](=[CH:7][C:6]([C:25]3[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=3[C:27]#[N:28])=[CH:14][CH:13]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 162722-BromobenzonitrileHCID 225031985-Tributylstannanyl-indan-1-one

Product 1

HCID 190089072-(1-Oxo-indan-5-yl)-benzonitrileYield 53.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-tributylstannanyl-indan-1-one (2.25 grams, 5.8 mmol), 2-bromobenzonitrile (1.06 grams, 5.8 mmol) and PdCl2 (PPh3)2 (421 mg, 0.6 mmol) was heated in dioxane (15 mL) for 20 hours. The reaction was cooled to room temperature, concentrated in vacuo and transferred to a SiO2 -gel column. Flash chromatography using a gradient of 25% ethyl acetate/hexanes to 50% ethyl acetate/hexanes yielded 725 mg of a colorless solid. 1H NMR (250 MHz, CDCl3): d 7.9 (d, 1 H), 7.8 (d, 1 H), 7.69 (m, 2 H), 7.54 (m, 3 H), 3.24 (t, 2 H), 2.78 (t, 2 H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8325f58bc4e647c7bf888f7e9c18ee93
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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