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

HRID 1519627Notes

Reaction equation

HRID 1519627 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1.[Li+].[Cl-].[CH2:13]([Sn](CCCC)(CCCC)CCCC)[CH:14]=[CH2:15]>C1(C)C=CC=CC=1.CCOC(C)=O.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>[CH2:15]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1)[CH:14]=[CH2:13]

Participants

7

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 7360294-Bromo-2-fluorobenzonitrile

Product 1

HCID 247217663-(4-Cyano-3-fluorophenyl)-1-propene

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromo-2-fluorobenzonitrile (5.0 g, 13 mmol) in 100 ml of toluene was added LiCl (1.7 g, 39 mmol), Pd(PPh3)4 (400 mg), Allyl tributyltin (5.2 g, 16 mmol), and then the mixture was heated to reflux overnight. After the reaction was completed, the reaction solution was diluted with EtOAc and filtered. The filtrate was concentrated and purified with silica gel column chromatograph to give crude 4-allyl-2-fluorobenzonitrile.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified with silica gel column chromatograph

Sources & evidence

ORD record
ord-6223a6ff3b2544d99f8a85a3b0741f59
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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