4-Bromo-2,6-difluorobenzonitrile → 2,6-Difluoro-4-vinylbenzonitrile

HRID 1502071Notes

Reaction equation

HRID 1502071 reaction equation
Br[C:2]1[CH:9]=[C:8]([F:10])[C:5]([C:6]#[N:7])=[C:4]([F:11])[CH:3]=1.[CH:12](C1C=CC(C#N)=C(OC)C=1C)=[CH2:13]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:10][C:8]1[CH:9]=[C:2]([CH:12]=[CH2:13])[CH:3]=[C:4]([F:11])[C:5]=1[C:6]#[N:7]

Participants

4

Reactant 2

HCID 27569164-Bromo-2,6-difluorobenzonitrileHCID 666472914-Ethenyl-3-methyl-2-(methyloxy)benzonitrile

Product 1

HCID 896190062,6-Difluoro-4-vinylbenzonitrile

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

2,6-Difluoro-4-vinylbenzonitrile was prepared from 4-bromo-2,6-difluorobenzonitrile using potassium vinyl trifluoroborate and PdCl2(dppf)2 in an analagous fashion as described for 4-ethenyl-3-methyl-2-(methyloxy)benzonitrile above.

Sources & evidence

ORD record
ord-fd99baf18d624cd682a48cb97c3d95ee
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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