Sodium Carbonate → 2-Chloro-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-amine

HRID 405243

Reaction equation

HRID 405243 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[Cl:9].[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=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:15]1[CH:16]=[CH:17][C:12]([C:11]([F:22])([F:21])[F:10])=[CH:13][CH:14]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 888884-Bromo-3-chloroanilineHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 688342842-Chloro-4'-(trifluoromethyl)-[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

Conditions

Temperature
90 °C

Procedure

4-bromo-3-chloroaniline (2.1 g, 10.2 mmol), (4-(trifluoromethyl)phenyl)boronic acid (2.7 g, 14.2 mmol), Pd(dppf)Cl2 (744 mg, 1.0 mmol), 2M aqueous Na2CO3 (15.3 mL, 30.5 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, was 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-d72259e8bf7c48729e74a335ef3854e4
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Linked notes

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