4-Iodoaniline → 4-(3,4-Difluorophenyl)aniline

HRID 405217Notes

Reaction equation

HRID 405217 reaction equation
I[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[F:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][C:15]=1[F:16].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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:11]=[C:12]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=2)[CH:13]=[CH:14][C:15]=1[F:16]

Participants

6

Reactant 3

HCID 108934-IodoanilineHCID 11430Potassium CarbonateHCID 27343373,4-Difluorobenzeneboronic acid

Product 1

HCID 610262874-(3,4-Difluorophenyl)aniline

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

4-Iodoaniline (800 mg, 3.7 mmol), (3,4-difluorophenyl)boronic acid (1.2 g, 7.3 mmol), Pd(dppf)Cl2 (267 mg, 0.4 mmol), and 2M aqueous K2CO3 (3.7 mL, 7.3 mmol) were dissolved in 1,4-dioxane (15 mL) and heated to 80° C. After 2 h the resulting mixture was cooled to room temperature and the layers were separated. The organic phase was concentrated and purified via column chromatography to yield the title compound.

Workup

  1. temperatureAfter 2 h the resulting mixture was cooled to room temperature
  2. customthe layers were separated
  3. concentrationThe organic phase was concentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-f8d2841087064ea984a5fa0bad3b90cb
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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