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

HRID 405243

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-d72259e8bf7c48729e74a335ef3854e4
Quelldatensatz: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08748624B2

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