Undecane → 2-Nitro-4-trifluoromethyl-biphenyl

HRID 2358813Notes

Reaction equation

HRID 2358813 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCCCCCCCCCC>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[N+:12]([C:3]1[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([O-:14])=[O:13]

Participants

7

Reactant 3

HCID 14257UndecaneHCID 66827Phenylboronic AcidHCID 5207064-Bromo-3-nitrobenzotrifluoride

Product 1

HCID 113001192-Nitro-4-trifluoromethyl-biphenyl

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Commercially available 1-bromo-2-nitro-4-trifluoromethyl-benzene (0.130 g, 0.48 mmol) was reacted with phenylboronic acid (0.072 g, 0.59 mmol) as described in Example 213a substituting dioxane for toluene, bis(triphenylphosphine)-palladium (II) chloride for palladium acetate and omitting the 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3.]undecane. The reaction was complete after three hours and the title biphenyl recovered in quantitative yield, sufficiently pure for use as isolated.

Workup

  1. customthe title biphenyl recovered in quantitative yield, sufficiently pure for use
  2. customas isolated

Sources & evidence

ORD record
ord-77834930184347f2ac2f1c9f61c0c659
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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