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

HRID 405143Notes

Reaction equation

HRID 405143 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[F:9][C:10]1[CH:15]=[C:14]([F: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]>[F:9][C:10]1[CH:15]=[C:14]([F: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 78074-BromoanilineHCID 11430Potassium CarbonateHCID 27343342,4-Difluorophenylboronic acid

Product 1

HCID 27582662',4'-Difluoro-[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-Bromoaniline (2.0 g, 11.6 mmol), (2,4-difluorophenyl)boronic acid (2.1 g, 13.4 mmol), Pd(dppf)Cl2 (952 mg, 1.2 mmol), and K2CO3 (3.2 g, 23.3 mmol) were dissolved in 1,4-dioxane (80 mL) and water (20 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-9a3e206ab96f41d1ae5a0461b8a6ba76
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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