Sodium Carbonate → 3-Fluoro-5-methoxy-[1,1'-biphenyl]-4-carbonitrile

HRID 922389Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 922389
Br[C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:5]([C:6]#[N:7])=[C:4]([F:12])[CH:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.CCOC(C)=O>[F:12][C:4]1[CH:3]=[C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=[C:8]([O:10][CH3:11])[C:5]=1[C:6]#[N:7]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 574422094-Bromo-2-fluoro-6-methoxybenzonitrile

Produkt 1

HCID 867193543-Fluoro-5-methoxy-[1,1'-biphenyl]-4-carbonitrileAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 4-bromo-2-fluoro-6-methoxybenzonitrile (2, 5.22 g, 22.7 mmol), phenylboronic acid (4.15 g, 34 mmol) and 2 M Na2CO3 (23 mL) in toluene (100 mL) was purged with N2 for 10 min. Pd(PPh4)3 (2.62 g, 27.7 mmol) and EtOH (5 drops) were added. The mixture was then heated under N2 in a sealed tube at 80° C. for 18 h. The mixture was cooled to room temperature, diluted with EtOAc (300 mL), filtered through celite, concentrated and purified by silica gel chromatography eluting with ethyl acetate in hexane (0-100%) to afford the title compound (5.05 g, 97%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 7.57-7.55 (m, 2H), 7.50-7.23 (m, 3H), 7.01-6.99 (m, 1H), 6.93 (s, 1H), 3.95 (s, 3H).

Aufarbeitung

  1. customwas purged with N2 for 10 min
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through celite,
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography
  6. washeluting with ethyl acetate in hexane (0-100%)

Quellen und Nachweise

ORD-Eintrag
ord-45247b0850884ec0865cfe97db91ac0b
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278940B2

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