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

Reaction equation

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

Participants

Reactant 2

HCID 936542-Bromo-5-fluorobenzonitrile

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

Product 1

HCID 112424114,2'-Difluoro-5'-nitrobiphenyl-2-carbonitrile

Procedure

2-Bromo-5-fluorobenzonitrile was coupled to 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane as described in Example 2 to give 4,2′-difluoro-5′-nitrobiphenyl-2-carbonitrile as a black solid: δH (360 MHz, CDCl3) 7.38-7.56 (4H, m), 8.33-8.40 (2H, m).

Sources & evidence

ORD record: ord-244259e79f2a4190a8f6dc8f5dba5c5d
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279580B2

Reaction notes

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