Allyltributylstannane → 3-(3-Cyano-4-fluorophenyl)-1-propene

HRID 2173227Notes

Reaction equation

HRID 2173227 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[CH2:11]([Sn](CCCC)(CCCC)CCCC)[CH:12]=[CH2:13].[Li+].[Cl-]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:10][C:5]1[CH:4]=[CH:3][C:2]([CH2:13][CH:12]=[CH2:11])=[CH:9][C:6]=1[C:7]#[N:8]

Participants

6

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 247217703-(3-Cyano-4-fluorophenyl)-1-propene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of compound 5-bromo-2-fluorobenzonitrile (2.5 g, 12.5 mmol), allyl-tributyl-stannane (4.97 g, 12.5 mmol), LiCl (1.6 g, 37.5 mmol) and Pd(PPh3)4 (0.2 g) in anhydrous toluene was refluxed under N2 overnight. Distilled the solution under reduce pressure and the residue was purified with silica gel cloumn chromatography to give the product 2-fluoro-5-(prop-2-en-1-yl)benzonitrile.

Workup

  1. temperaturewas refluxed under N2 overnight
  2. distillationDistilled the solution
  3. customthe residue was purified with silica gel cloumn chromatography

Sources & evidence

ORD record
ord-19fbc7f826694914b29846a941630961
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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