Undecane → 2-Nitro-4-trifluoromethyl-biphenyl

HRID 2197978Notes

Reaction equation

HRID 2197978 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-ee885539577b40889c953c456059a234
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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