Allyltributylstannane → HCID 67515716, compound

HRID 2173233Notes

Reaction equation

HRID 2173233 reaction equation
Br[C:2]1[C:3]([O:11][CH3:12])=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[CH2:13]([Sn](CCCC)(CCCC)CCCC)[CH:14]=[CH2:15].[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]=[C:3]([O:11][CH3:12])[C:2]([CH2:15][CH:14]=[CH2:13])=[CH:9][C:6]=1[C:7]#[N:8]

Participants

6

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 67515500HCID 67515500, compound

Product 1

HCID 67515716HCID 67515716, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of compound 5-bromo-2-fluoro-4-methoxybenzonitrile (10.0 mmol), allyl-tributyl-stannane (12.0 mmol), LiCl (20.0 mmol) and Pd(PPh3)4 (0.2 g) in anhydrous toluene was refluxed under N2 overnight. Distilled off the solvent under reduce pressure, the residue was purified with silica gel cloumn chromatography to give the product 2-fluoro-4-methoxy-5-(prop-2-en-1-yl)benzonitrile.

Workup

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

Sources & evidence

ORD record
ord-00822376fab04769a98cce051b83561d
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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