Sodium Bicarbonate → 4'-Fluoro-2'-methoxy-3-trifluoromethyl-biphenyl-4-carbonitrile

HRID 585581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 585581
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.C([O-])(O)=O.[Na+].[F:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[C:22]([O:29][CH3:30])[CH:21]=1>C1(C)C=CC=CC=1.CCO.[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=2)=[C:22]([O:29][CH3:30])[CH:21]=1

Komponenten

8

Edukt 3

HCID 516892Sodium BicarbonateHCID 2782672(4-Fluoro-2-methoxyphenyl)boronic acidHCID 223378254-Bromo-2-(trifluoromethyl)benzonitrile

Produkt 1

HCID 223378244'-Fluoro-2'-methoxy-3-trifluoromethyl-biphenyl-4-carbonitrileAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

In a round bottom flask under argon, 4-bromo-2-trifluoromethylbenzonitrile (1 g, 4 mmol) was solubilized in a mixture of toluene (55 mL) and EtOH (20 mL). Aq. NaHCO3 (20 ml, 5 eq., 0.8 M solution) and 4-fluoro-2-methoxyphenylboronic acid (816 mg, 4.8 mmol) were added. The mixture was degassed under the stream of argon for 10 min. Then Pd(PPh3)4 (462 mg, 0.4 mmol) was added and the mixture was heated at 95° C. for 2 hr. After it was cooled, the mixture was poured in brine and extracted with CH2Cl2. This organic layer was dried (MgSO4), filtered and evaporated. Chromatography on a silica gel (250 ml, EtOAc:hexanes, 1:9), gave a white solid (951 mg, 81%), 1H NM (300 MHz, acetone-d6)δ: 8.02-8.14 (m, 3H, C2,5,6—H), 7.53 (dd, 1H, J=8, 7 Hz, C6′—H), 7.03 (dd, 1H, J=11, 2 Hz, C3′—H), 6.89 (td, 1H, J=8, 2Hz, C5′—H).

Aufarbeitung

  1. customThe mixture was degassed under the stream of argon for 10 min
  2. temperatureAfter it was cooled
  3. extractionextracted with CH2Cl2
  4. dry with materialThis organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-5e9422330af34dbcacaf82cbaef32e18
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06933321B2

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