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

HRID 1061764Notes

Reaction equation

HRID 1061764 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 was coupled with 3-nitrophenylboronic acid by the method of Example 7, part c) to yield 4-fluoro-3′-nitrobiphenyl-2-carbonitrile, which was reduced to 3′-amino-4-fluorobiphenyl-2-carbonitrile by the method of Example 5, part b). This was converted into 4-fluoro-3′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile as described in Example 7 parts e) and f), using bis(pinacolato)diboron instead of bis(neopentyl glycolato)diboron. The product was isolated as a brown oil which solidified on standing. δH (400 MHz, CDCl3) 1.36 (12H, s), 7.35 (1H, td, J 8.2 and 2.7), 7.44-7.54 (3H, m), 7.65 (1H, dt, J 8.2 and 1.7), 7.88-7.90 (2H, m)

Sources & evidence

ORD record
ord-252de4ba92034f9c8cef4fcd6d19eedb
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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