2-Bromobenzonitrile → 2'-Fluoro-5'-nitrobiphenyl-2-carbonitrile

HRID 1180224Notes

Reaction equation

HRID 1180224 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[F:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1B1OC(C)(C)C(C)(C)O1>>[F:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1[C:2]1[C:3]([C:4]#[N:5])=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 162722-BromobenzonitrileHCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol ester

Product 1

HCID 114478612'-Fluoro-5'-nitrobiphenyl-2-carbonitrileYield 100%

Procedure

A mixture of 2-bromobenzonitrile (34.6 g, 190 mmol) and 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (76.1 g, 285 mmol) were coupled as described in Example 2 to afford 2′-fluoro-5′-nitrobiphenyl-2-carbonitrile as a beige solid (46 g, 100%): δH (360 MHz, CDCl3) 7.37-7.42 (1H, m), 7.53 (1H, d, J 8), 7.59 (1H, td, J 8 and 1), 7.75 (1H, td, J 8 and 1), 7.83 (1H, dd, J 8 and 1), 8.35-8.39 (2H, m).

Sources & evidence

ORD record
ord-75b776cfbed94de1b048a527e308c3d6
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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