Sodium Carbonate → 1-(3-Methyl-4'-nitro-1,1'-biphenyl-4-yl)ethanone

HRID 9558

Reaktionsgleichung

Reaktionsgleichung von HRID 9558
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[C:9]([CH3:16])[CH:8]=1)(=O)=O.[N+:19]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)([O-:21])=[O:20].C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1(C)C=CC=CC=1>[CH3:16][C:9]1[CH:8]=[C:7]([C:25]2[CH:26]=[CH:27][C:22]([N+:19]([O-:21])=[O:20])=[CH:23][CH:24]=2)[CH:12]=[CH:11][C:10]=1[C:13](=[O:15])[CH3:14]

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27735524-Nitrophenylboronic acidHCID 114829354-Acetyl-3-methylphenyl trifluoromethanesulfonate

Produkt 1

HCID 219857981-(3-Methyl-4'-nitro-1,1'-biphenyl-4-yl)ethanoneAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 4-acetyl-3-methylphenyl trifluoromethanesulfonate (6.90 g, 24.0 mmol), 4-nitrophenylboronic acid (3.80 g, 24 mmol), 2 N aqueous sodium carbonate (88.0 mL), dioxane (88.0 mL), and toluene (296 mL) was purged with argon for 30 minutes before [1,1′-bis(diphenyl-phosphino)-ferrocene]dichloro palladium(II) (1:1 complex with dichloromethane, 1.90 g, 2.30 mmol) was added. The reaction mixture was heated at 85° C. and stirred overnight. The layers were separated and the organic layer was washed with water (2×50 mL), dried over magnesium sulfate, and concentrated under reduced pressure to give a dark brown oil. This material was purified by flash chromatography (7 to 20% ethyl acetate/hexane) to give 1-(3-methyl-4′-nitro-1,1′-biphenyl-4-yl)ethanone as a light yellow solid (6.12 g, 99% yield). GC-MS m/z 255 (M+), ret. time 9.89 min; 1H NMR (CDCl3) δ: 2.61 (s, 3H), 2.62 (s, 3H), 7.49–55 (m, 2H), 7.78 (d, 2H), 7.81 (d, 1H), 8.32 (d, 2H).

Aufarbeitung

  1. additionwas added
  2. customThe layers were separated
  3. washthe organic layer was washed with water (2×50 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a dark brown oil
  7. customThis material was purified by flash chromatography (7 to 20% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4b8faee746e147b69f20751ab4e1c852
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091228B2

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