Ethanol → Methyl 5'-fluoro-2'-nitrobiphenyl-2-carboxylate

HRID 238070

Reaktionsgleichung

Reaktionsgleichung von HRID 238070
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1B(O)O)=[O:4].Br[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23].C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.C(O[Pd]OC(=O)C)(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[F:21][C:19]1[CH:18]=[CH:17][C:16]([N+:22]([O-:24])=[O:23])=[C:15]([C:6]2[C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:20]=1

Komponenten

8

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27569932-Bromo-4-fluoro-1-nitrobenzeneHCID 27734962-(Methoxycarbonyl)benzeneboronic acid

Produkt 1

HCID 67296936Methyl 5'-fluoro-2'-nitrobiphenyl-2-carboxylateAusbeute 56,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a microwave vessel was added 2-(methoxycarbonyl)phenylboronic acid (63.4 mg, 0.352 mmol), 2-bromo-4-fluoro-1-nitrobenzene (77 mg, 0.35 mmol), diacetoxypalladium (0.93 mg, 4.1 mmol) and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (3.47 mg, 8.45 μmol). Ethanol (1760 μl) and sodium carbonate (176 μl, 0.352 mmol) were added and the mixture was reacted in a microwave reactor at 100° C. for 30 min. The reaction mixture was diluted with dichloromethane, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography (eluant: 9:1 hexane/ethyl acetate) to provide methyl 5′-fluoro-2′-nitrobiphenyl-2-carboxylate (37a, 54.8 mg, 0.199 mmol, 56.6% yield).

Aufarbeitung

  1. customthe mixture was reacted in a microwave reactor at 100° C. for 30 min
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative thin layer chromatography (eluant: 9:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-22c50defc4af4bc28e5d4aa5c8b43360
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642538B2

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