4-Chloroanisole → Ethyl 4'-methoxy[1,1'-biphenyl]-4-carboxylate

HRID 607811

Reaction equation

HRID 607811 reaction equation
CCOC(=O)c1ccc(B(O)O)cc1.COc1ccc(Cl)cc1>C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.C1COCCO1.CC(C)(C)P(C1CCCCC1)C1CCCCC1.O.O=P([O-])([O-])[O-].[K+].[K+].[K+].[Ni]>CCOC(=O)c1ccc(-c2ccc(OC)cc2)cc1

Participants

8

Reactant 2

HCID 121674-ChloroanisoleHCID 27343504-Ethoxycarbonylphenylboronic acid

Product 1

HCID 2764348Ethyl 4'-methoxy[1,1'-biphenyl]-4-carboxylateYield 1%

Reagents, catalysts & solvents 5

HCID 962WaterReagentHCID 62657Potassium Phosphate, TribasicReagentHCID 4643319tert-ButyldicyclohexylphosphineCatalystHCID 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-9f1f8542026340eea3c3d13d80252892
Source dataset
Ni-catalyzed Suzuki Miyaura cross-coupling
Original link
View source

Linked notes

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