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

HRID 1180234Notes

Reaction equation

HRID 1180234 reaction equation
Br[C:2]1[C:9]([F:10])=[CH:8][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:9]1[CH:8]=[CH:7][CH:6]=[C:3]([C:4]#[N:5])[C:2]=1[C:13]1[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=1[F:11]

Participants

3

Reactant 2

HCID 27833932-Bromo-3-fluorobenzonitrileHCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol ester

Product 1

HCID 116875426,2'-Difluoro-5'-nitrobiphenyl-2-carbonitrile

Procedure

2-Bromo-3-fluorobenzonitrile (2.50 g, 12.5 mmol) was coupled to 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane as described in Example 2 to give 6,2′-difluoro-5′-nitrobiphenyl-2-carbonitrile as a black solid: δH (400 z, CDCl3) 7.40-7.44 (1H, m), 7.47-7.52 (1H, m), 7.59-7.67 (2H, m), 8.37-8.44 (2H, m).

Sources & evidence

ORD record
ord-871bafce52bc4d5195c41343862615ea
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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