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

Participants

Reaction Steps

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)

Provenance & Evidence