Phenylboronic Acid → 2-Cyano-3-fluorobiphenyl

HRID 1817739Notes

Reaction equation

HRID 1817739 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](I)[C:3]=1[C:4]#[N:5].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(C)C=CC=CC=1.CCO.O>COCCOC.O>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 66827Phenylboronic AcidHCID 5227222-Fluoro-6-iodobenzonitrileHCID 86587398Ethanol toluene water

Product 1

HCID 235096522-Cyano-3-fluorobiphenyl

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

The desired productwas prepared by substituting 2-fluoro-6-iodobenzonitrile for Example 1A and phenylboronic acid for Example 1B in Example 1C. Additionally, toluene/EtOH/H2O (3:2:1) was substituted for DME/H2O as the solvent.

Workup

  1. customThe desired productwas prepared

Sources & evidence

ORD record
ord-55a44797efbd4002902c143117c373d1
Source dataset
uspto-grants-2009_10
Patent number
US07598283B2

Reaction notes

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