Sodium Carbonate → 3-Chloro-4-(4-chlorophenyl)benzenamine

HRID 2167146Notes

Reaction equation

HRID 2167146 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[Cl:9].[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>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:3]1[CH:4]=[C:5]([NH2:6])[CH:7]=[CH:8][C:2]=1[C:14]1[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 888884-Bromo-3-chloroaniline

Product 1

HCID 198789103-Chloro-4-(4-chlorophenyl)benzenamine

Reagents, catalysts & solvents 3

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

Conditions

Temperature
90 °C

Procedure

4-Bromo-3-chloroaniline (2.0 g, 9.7 mmol), (4-chlorophenyl)boronic acid (2.0 g, 12.7 mmol), Pd(dppf)Cl2 (713 mg, 1.0 mmol), 2M aqueous Na2CO3 (12.2 mL, 24.4 mmol) were dissolved in 1,4-dioxane (30 mL) and the resulting mixture was heated to 90° C. After 16 h the resulting mixture was cooled to room temperature, then diluted with EtOAc, washed with water and brine. The organic layer was dried (Na2SO4), concentrated and diethyl ether was added. The resulting precipitate was filtered and dried in vacuo to yield the title compound.

Workup

  1. temperatureAfter 16 h the resulting mixture was cooled to room temperature
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. additiondiethyl ether was added
  6. filtrationThe resulting precipitate was filtered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-b82b25232f6d4ccfb3520a62e5b72742
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

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