m-Chloroperbenzoic acid → 2,6-Difluoro-4-(oxiran-2-yl)benzonitrile

HRID 1502072Notes

Reaction equation

HRID 1502072 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH:10]=[CH2:11])[CH:7]=[C:6]([F:12])[C:3]=1[C:4]#[N:5].C1C=C(Cl)C=C(C(OO)=[O:21])C=1.FC1C(C2CO2)=CC(OC)=C(C=1)C#N>>[F:1][C:2]1[CH:9]=[C:8]([CH:10]2[CH2:11][O:21]2)[CH:7]=[C:6]([F:12])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 866473025-Fluoro-2-methoxy-4-oxiran-2-ylbenzonitrileHCID 896190062,6-Difluoro-4-vinylbenzonitrile

Product 1

HCID 896190212,6-Difluoro-4-(oxiran-2-yl)benzonitrile

Procedure

2,6-Difluoro-4-(oxiran-2-yl)benzonitrile was prepared from 2,6-Difluoro-4-vinylbenzonitrile using m-CPBA in an analagous fashion to that described for 5-fluoro-2-methoxy-4-(oxiran-2-yl)benzonitrile (Step H) above: 1H NMR (500 MHz, CDCl3) δ 7.02 (d, J=8.0 Hz, 2H), 3.92 (dd, J=3.6, 2.4 Hz, 1H), 3.24 (dd, J=5.4, 4.0 Hz, 1H), 2.74 (dd, J=5.4, 2.4 Hz, 1H).

Sources & evidence

ORD record
ord-2c420bf6969c49e9a43185b574cad92b
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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