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

HRID 405120Notes

Reaction equation

HRID 405120 reaction equation
I[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1B(O)O.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:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 108934-IodoanilineHCID 11430Potassium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acid

Product 1

HCID 99647252',4'-Dichloro-[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

4-Iodoaniline (10.0 g, 45.7 mmol), (2,4-dichlorophenyl)boronic acid (10.5 g, 54.8 mmol), Pd(dppf)Cl2 (3.7 g, 4.6 mmol), and K2CO3 (12.6 g, 91.3 mmol) were dissolved in 1,4-dioxane (200 mL) and water (50 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-363d567b53694b038b6c0aaf6503ddc2
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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