3-Bromo-4-fluorobenzonitrile → HCID 22285290, compound

HRID 1061818Notes

Reaction equation

HRID 1061818 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[C:5]#[N:6].[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[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:3][C:4]([C:5]#[N:6])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 1235793-Bromo-4-fluorobenzonitrileHCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol ester

Product 1

HCID 22285290HCID 22285290, compoundYield 100%

Procedure

3-Bromo-4-fluorobenzonitrile (2.00 g, 10 mmol) was coupled to 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (4.01 g, 15 mmol) following the procedure described in Example 14 part a), affording 6,2′-difluoro-5′-nitrobiphenyl-3-carbonitrile as a brown solid (2.60 g, 100%). δH (360 MHz, CDCl3) 7.38 (2H, q, J 8.8), 7.77-7.82 (2H, m), 8.33-8.38 (2H, m).

Sources & evidence

ORD record
ord-f43762b3e7c3459a859f99cc1d066e1f
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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