1-Bromo-2-fluorobenzene → 5-(2-Fluorophenyl)-1-methylimidazole-4-carbonitrile

HRID 1934041Notes

Reaction equation

HRID 1934041 reaction equation
Cn1cnc(C#N)c1.Fc1ccccc1Br>C=C[CH2-].C=C[CH2-].CC(=O)[O-].CCCCOC(C)=O.C[C@]12C[C@@]3(C)O[C@](C)(C[C@@](C)(O1)P3c1ccccc1)O2.[Cl][Pd+].[Cl][Pd+].[K+]>Cn1cnc(C#N)c1-c1ccccc1F

Participants

9

Reactant 2

HCID 612591-Bromo-2-fluorobenzeneHCID 27951151-Methyl-1H-imidazole-4-carbonitrile

Product 2

HCID 741954,4'-Bis(1,1-dimethylethyl)-1,1'-biphenylHCID 841174465-(2-Fluorophenyl)-1-methylimidazole-4-carbonitrileYield 16.83%

Reagents, catalysts & solvents 5

HCID 517044Potassium AcetateReagentHCID 61538Palladium, di-mu-chlorobis(eta3-2-propenyl)di-CatalystHCID 71669129HCID 71669129, compoundCatalystHCID 31272Butyl AcetateSolventHCID 741954,4'-Bis(1,1-dimethylethyl)-1,1'-biphenylInternal standard

Conditions

Temperature
90 °C

Workup

  1. additionThe plate was removed from the glovebox, opened, and diluted to a 900 uL total volume with N,N-dimethylacetamide. The plate was stirred for 5 min and a 75 uL sample was taken and filtered into an HPLC analysis plate. The filter was rinsed with 400 uL acetonitrile/water (4:1) solution and analyzed by UHPLCMS
  2. stirringNo procedure recorded
  3. aliquotNo procedure recorded
  4. filtrationKeep organic

Sources & evidence

ORD record
ord-872a6c677ddc4f5a89aa40df3046e195
Source dataset
Shields Arylation

Reaction notes

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