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

HRID 130009

Reaction equation

HRID 130009 reaction equation
Cn1cnc(C#N)c1.Fc1ccccc1Br>C=C[CH2-].C=C[CH2-].CC(=O)N(C)C.CC(C)(C)C(=O)[O-].[Cl][Pd+].[Cl][Pd+].[K+].c1ccc(P(c2ccccc2)C2CCCCC2)cc1>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 44.61%

Reagents, catalysts & solvents 5

HCID 23662159Potassium TrimethylacetateReagentHCID 61538Palladium, di-mu-chlorobis(eta3-2-propenyl)di-CatalystHCID 80756Phosphine, cyclohexyldiphenyl-CatalystHCID 31374DimethylacetamideSolventHCID 741954,4'-Bis(1,1-dimethylethyl)-1,1'-biphenylInternal standard

Conditions

Temperature
105 °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-9b01b7df80134acea9f7badc34be1c5f
Source dataset
Shields Arylation

Linked notes

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