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

HRID 607914

Reaction equation

HRID 607914 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.C1COCCO1.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.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 17%

Reagents, catalysts & solvents 5

HCID 962WaterReagentHCID 62657Potassium Phosphate, TribasicReagentHCID 6433264Bis(1,5-cyclooctadiene)nickelCatalystHCID 44597232Bis(3,5-bis(trifluoromethyl)phenyl)(3,6-dimethoxy-2',4',6'-tri(propan-2-yl)(1,1'-biphenyl)-2-yl)phosphaneCatalystHCID 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-0a99f730b8204d8289f51a940398a1f9
Source dataset
Ni-catalyzed Suzuki Miyaura cross-coupling
Original link
View source

Linked notes

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