3-Nitrophenylboronic Acid → 4-Fluoro-3'-nitrobiphenyl-2-carbonitrile

HRID 586263Notes

Reaction equation

HRID 586263 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[C:4]#[N:5].[N+:11]([C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)([O-:13])=[O:12]>>[F:10][C:7]1[CH:6]=[C:3]([C:4]#[N:5])[C:2]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:11]([O-:13])=[O:12])[CH:19]=2)=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 16773-Nitrophenylboronic AcidHCID 936542-Bromo-5-fluorobenzonitrile

Product 1

HCID 222853434-Fluoro-3'-nitrobiphenyl-2-carbonitrile

Procedure

2-Bromo-5-fluorobenzonitrile and 3-nitrophenylboronic acid were coupled following the procedure in Example 4 to afford 4-fluoro-3′-nitrobiphenyl-2-carbonitrile as a black solid: 1H NMR (360 MHz, CDCl3) δ 7.39-7.48 (2H, m), 7.52-7.64 (1H, m), 7.71 (1H, dd, J 8, 8 Hz), 7.89 (1H, d, J 8 Hz), 8.33-8.37 (2H, m).

Sources & evidence

ORD record
ord-25adf9fde7434b10ac391e710fd0dcd4
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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