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

HRID 1934124Notes

Reaction equation

HRID 1934124 reaction equation
Cn1cnc(C#N)c1.Fc1ccccc1Br>C=C[CH2-].C=C[CH2-].CC(=O)[O-].CCCC#N.COc1ccc(OC)c(P(c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.[Cl][Pd+].[Cl][Pd+].[Cs+]>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 32.74%

Reagents, catalysts & solvents 5

HCID 5152919Cesium acetateReagentHCID 61538Palladium, di-mu-chlorobis(eta3-2-propenyl)di-CatalystHCID 44597232Bis(3,5-bis(trifluoromethyl)phenyl)(3,6-dimethoxy-2',4',6'-tri(propan-2-yl)(1,1'-biphenyl)-2-yl)phosphaneCatalystHCID 8008ButyronitrileSolventHCID 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-265be472f6624610bceb76fb449f2639
Source dataset
Shields Arylation

Reaction notes

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