Potassium Carbonate → 4'-Chloro-2-methyl-[1,1'-biphenyl]-4-amine

HRID 405193Notes

Reaction equation

HRID 405193 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.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]>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[CH3:9])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 233594-Bromo-3-methylanilineHCID 742994-Chlorophenylboronic acid

Product 1

HCID 600391884'-Chloro-2-methyl-[1,1'-biphenyl]-4-amine

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

4-bromo-3-methylaniline (5.1 g, 27.4 mmol), 4-chlorophenylboronic acid (5.1 g, 32.9 mmol), Pd(dppf)Cl2 (1.1 g, 1.4 mmol), and 2M aqueous K2CO3 (27.4 mL, 54.8 mmol) were dissolved in 1,4-dioxane (110 mL) and the resulting mixture was heated to 100° C. After 2 h the resulting mixture was cooled to room temperature, concentrated, diluted with EtOAc and 4M aqueous NaCl, and the layers were separated. The aqueous layer was extracted with EtOAc and the combined organics were dried (Na2SO4), 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. concentrationconcentrated
  3. additiondiluted with EtOAc and 4M aqueous NaCl
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with EtOAc
  6. dry with materialthe combined organics were dried (Na2SO4)
  7. concentrationconcentrated
  8. custompurified via column chromatography

Sources & evidence

ORD record
ord-68c8751463744f90910a9e1d1a9206fe
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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