2-Bromo-4-fluorobenzonitrile → 5,2'-Difluoro-5'-nitrobiphenyl-2-carbonitrile

HRID 2183967Notes

Reaction equation

HRID 2183967 reaction equation
Br[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][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:8]1[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]([C:4]#[N:5])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 1189392-Bromo-4-fluorobenzonitrileHCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol ester

Product 1

HCID 222852855,2'-Difluoro-5'-nitrobiphenyl-2-carbonitrile

Procedure

2-Bromo-4-fluorobenzonitrile was coupled to 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane as described in Example 51 to give 5,2′-difluoro-5′-nitrobiphenyl-2-carbonitrile as a black solid: δH (360 MHz, CDCl3) 7.25-7.33 (2H, m), 7.40-7.44 (1H, m), 7.86 (1H, dd, J 9 and 6), 8.35-8.42 (2H, m).

Sources & evidence

ORD record
ord-c4bdb519bf1645fa9fec6f256c95f8d7
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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