Water → HCID 22473582, compound

HRID 2183894Notes

Reaction equation

HRID 2183894 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Br-].[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Zn+])#[N:14].O>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]2[C:15]([C:13]#[N:14])=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 962WaterHCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 178509677HCID 178509677, compound

Product 1

HCID 22473582HCID 22473582, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-bromo-1-fluoro-2-nitrobenzene (9.68 g, 44 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.53 g, 1.3 mmol) was treated with 2-cyanophenylzinc bromide (100 ml of a 0.5M solution in tetrahydrofuran, 50 mmol) then heated under reflux for 8 h. After cooling to ambient temperature the reaction mixture was poured into water (1000 ml). After stirring for 30 min the resulting solid was collected by filtration and dried under vacuum over phosphorus pentoxide to afford 4′-fluoro-3′-nitrobiphenyl-2-carbonitrile as a tan solid (10.7 g, 100%) which was used without further purification.

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 8 h
  3. filtrationwas collected by filtration
  4. dry with materialdried under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-72b0a83eb0fc466cb0f994defea7aae4
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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