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4-Chloroanisole → 4-Methoxy-4'-trifluoromethyl-biphenyl

HRID 607643
Notes
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Reaction equation

HRID 607643 reaction equation
COc1ccc(Cl)cc1.OB(O)c1ccc(C(F)(F)F)cc1>C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.C1COCCO1.COc1ccc(C)c(-c2c(C(C)C)cc(C(C)C)cc2C(C)C)c1P(C(C)(C)C)C(C)(C)C.O.O=P([O-])([O-])[O-].[K+].[K+].[K+].[Ni]>COc1ccc(-c2ccc(C(F)(F)F)cc2)cc1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 2

HCID 121674-ChloroanisoleHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 112074784-Methoxy-4'-trifluoromethyl-biphenylYield 0%

Reagents, catalysts & solvents 5

HCID 962WaterReagentHCID 62657Potassium Phosphate, TribasicReagentHCID 6433264Bis(1,5-cyclooctadiene)nickelCatalystHCID 56641709(2',4'-Diisopropyl-3-methoxy-6-methyl-6'-propyl-2-biphenylyl)[bis(2-methyl-2-propanyl)]phosphineCatalystHCID 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-28b8f98a2d83484cbf97dac32b2d3ff7
Source dataset
Ni-catalyzed Suzuki Miyaura cross-coupling
DOI
10.26434/chemrxiv.14388557.v1
Original link
View source

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes