4-Chloroanisole → 4'-Methoxy-2,4,6-trimethylbiphenyl

HRID 607760

Reaction equation

HRID 607760 reaction equation
COc1ccc(Cl)cc1.Cc1cc(C)c(B(O)O)c(C)c1>C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.C1COCCO1.CCCCCCCCP(CCCCCCCC)CCCCCCCC.O.O=P([O-])([O-])[O-].[K+].[K+].[K+].[Ni]>COc1ccc(-c2c(C)cc(C)cc2C)cc1

Participants

8

Reactant 2

HCID 121674-ChloroanisoleHCID 2921842,4,6-Trimethylbenzeneboronic acid

Product 1

HCID 108788734'-Methoxy-2,4,6-trimethylbiphenylYield 6%

Reagents, catalysts & solvents 5

HCID 962WaterReagentHCID 62657Potassium Phosphate, TribasicReagentHCID 20851TrioctylphosphineCatalystHCID 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-09d62334403d4df0adcb2e79f2f2be86
Source dataset
Ni-catalyzed Suzuki Miyaura cross-coupling
Original link
View source

Linked notes

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