1-Chloro-4-(trifluoromethyl)benzene → 4-Methoxy-4'-trifluoromethyl-biphenyl

HRID 607907Notes

Reaction equation

HRID 607907 reaction equation
COc1ccc(B(O)O)cc1.FC(F)(F)c1ccc(Cl)cc1>C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.C1CCC(P(C2CCCC2)C2CCCC2)C1.C1COCCO1.O.O=P([O-])([O-])[O-].[K+].[K+].[K+].[Ni]>COc1ccc(-c2ccc(C(F)(F)F)cc2)cc1

Participants

8

Reactant 2

HCID 73941-Chloro-4-(trifluoromethyl)benzeneHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 112074784-Methoxy-4'-trifluoromethyl-biphenylYield 37%

Reagents, catalysts & solvents 5

HCID 962WaterReagentHCID 62657Potassium Phosphate, TribasicReagentHCID 4463278Phosphine, tricyclopentyl-CatalystHCID 6433264Bis(1,5-cyclooctadiene)nickelCatalystHCID 312751,4-DioxaneSolvent4×

Conditions

Temperature
60 °C

Procedure

pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

Workup

  1. additionDilute with acetonitrile
  2. aliquotNo procedure recorded
  3. customDiluent solution was made in 1 L batches with 950 mL acetonitrile, 25 mL water, 25 mL glacial acetic acid, and 53 mg 4,4’-di-tert-butylbiphenyl as an external standard (0.2 equiv standard per reaction). Aliquot taken from each well (47 ul) is added into 753 ul of diluent solution

Sources & evidence

ORD record
ord-1144dc47231b4fd3bfb897158b7e34d5
Source dataset
Ni-catalyzed Suzuki Miyaura cross-coupling
Original link
View source

Reaction notes

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