3-Fluoro-5-methoxy-4-nitrobenzonitrile → 2-Fluoro-3-methoxy-4-nitrobenzonitrile

Reaction equation

F[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:13][CH3:14])[C:9]=1[N+:10]([O-:12])=[O:11])[C:5]#[N:6].BrC1C=CC([N+]([O-])=O)=C(OC)C=1[F:27]>>[F:27][C:7]1[C:8]([O:13][CH3:14])=[C:9]([N+:10]([O-:12])=[O:11])[CH:2]=[CH:3][C:4]=1[C:5]#[N:6]

Participants

Reactant 2

HCID 579555403-Fluoro-5-methoxy-4-nitrobenzonitrile2×

HCID 579555891-Bromo-2-fluoro-3-methoxy-4-nitrobenzene2×

Product 1

HCID 579555492-Fluoro-3-methoxy-4-nitrobenzonitrile

Procedure

The title compound was prepared according to the procedure for 3-fluoro-5-methoxy-4-nitrobenzonitrile (Compound 146F) using 1-Bromo-2-fluoro-3-methoxy-4-nitrobenzene (Compound 147G). 1H NMR (CDCl3, 400 MHz): δ=4.15 (d, J=2.27 Hz, 3H), 7.45 (dd, J=8.59, 5.56 Hz, 1H), 7.64 (dd, J=8.59, 1.77 Hz, 1H).

Sources & evidence

ORD record: ord-ffe9fbd631a84936bcfc6120c7d2f472
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399433B2

Reaction notes

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