2-Bromo-6-fluorobenzonitrile → 3,2'-Difluoro-5'-nitrobiphenyl-2-carbonitrile

HRID 1180238Notes

Reaction equation

HRID 1180238 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[C:4]#[N:5].[F:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1B1OC(C)(C)C(C)(C)O1>>[F:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([C:13]2[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=2[F:11])[C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 27831392-Bromo-6-fluorobenzonitrileHCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol ester

Product 1

HCID 222852823,2'-Difluoro-5'-nitrobiphenyl-2-carbonitrile

Procedure

2-Bromo-6-fluorobenzonitrile and 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane were coupled following the procedure in Example 2 to afford 3,2′-difluoro-5′-nitrobiphenyl-2-carbonitrile as a black solid: δH (360 MHz, CDCl3) 7.32-7.44 (3H, m), 7.71-7.77 (1H, m), 8.35-8.41 (2H, m).

Sources & evidence

ORD record
ord-1dd79d2c08344148bd1725d969ac912b
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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