Tetrafluorophthalonitrile → 2-Phenylpropionitrile

HRID 376515

Reaction equation

F[C:2]1[C:9](C#N)=[C:8](F)[C:7](F)=[C:6](F)[C:3]=1[C:4]#N.FC1C(F)=C(F)C(F)=C([C:19]#[N:20])C=1C#N.F[C:30]1C(F)=C(F)C=C(F)C=1C#N>>[CH3:30][CH:4]([C:19]#[N:20])[C:3]1[CH:2]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

Reactant 3

HCID 74600Tetrafluorophthalonitrile

HCID 608182Tetrafluoroisophthalonitrile2×

HCID 222875492,3,4,6-Tetrafluorobenzonitrile

Product 1

HCID 157612-Phenylpropionitrile

Procedure

By a method similar to Example 11, a reaction was carried out using 2,4,5,6-tetrafluoroisophthalonitrile, instead of 3,4,5,6-tetrafluorophthalonitrile. After 5 hours, the reaction solution was analyzed by gas chromatography, whereupon the conversion of 2,4,5,6-tetrafluoroisophthalonitrile was found to be 36% and the yield of 2,3,4,6-tetrafluorobenzonitrile (based on 2,4,5,6-tetrafluoroisophthalonitrile) was 20%. At the same time, 1.1 mmol of α-methylbenzylcyanide was produced. This corresponded to 0.35 times molar amount relative to the production of 2,3,4,6-tetrafluorobenzonitrile.

Sources & evidence

ORD record: ord-41e1ed2ba8da46c882cfa7d1e54ed6d9
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06020517

Linked notes

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