Water → 2,4'-Dichloro-2'-methyl-[1,1'-biphenyl]-4-amine

HRID 2167125Notes

Reaction equation

HRID 2167125 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1I)[NH2:5].[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[C:13]([CH3:20])[CH:12]=1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:5])[CH:6]=[CH:7][C:8]=1[C:14]1[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][C:13]=1[CH3:20]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2829263-Chloro-4-iodoanilineHCID 5017600(4-Chloro-2-methylphenyl)boronic acid

Product 1

HCID 866742052,4'-Dichloro-2'-methyl-[1,1'-biphenyl]-4-amine

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Chloro-4-iodoaniline (3.0 g, 11.8 mmol), (4-chloro-2-methylphenyl)boronic acid (2.4 g, 14.2 mmol), Pd(dppf)Cl2 (1.0 g, 1.2 mmol), and K2CO3 (3.3 g, 23.7 mmol) were dissolved in 1,4-dioxane (40 mL) and water (10 mL) and the resulting mixture was heated to 80° C. After 16 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry

Sources & evidence

ORD record
ord-b8a4e7c28d2a4390a2492c80ad4c8f0a
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

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