Sodium Carbonate → HCID 17965980, Verbindung

HRID 1348887

Reaktionsgleichung

Reaktionsgleichung von HRID 1348887
Cl[C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.Cl[Pd]Cl.C(O)C>[Cl:15][C:16]1[CH:21]=[C:20]([C:2]2[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=2)[CH:19]=[CH:18][CH:17]=1

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 83343Methyl 2-chloro-4-nitrobenzoateHCID 2734323(3-Chlorophenyl)boronic acid

Produkt 1

HCID 17965980HCID 17965980, VerbindungAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11050900Dichlorobis(tricyclohexylphosphine)pallium (II)KatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of methyl 2-chloro-4-nitrobenzoate (0.432 g, 2.0 mmol), 3-chlorophenylboronic acid (0.375 g, 2.4 mmol), trans-dichlorobis(tricyclohexylphosphine)-palladium (II) (0.074 g, 0.1 mmol), and sodium carbonate (0.64 g, 6.0 mmol) in a mixture of toluene (10 mL), dioxane (10 mL), and ethanol (2 mL) was heated to reflux for 12 hours, cooled to room temperature, diluted with ethyl acetate (10 mL), washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 1:10 ethyl acetate/hexanes to provide 0.58 g (99%) of the desired product. MS (DCI/NH3) m/z 309 (M+NH4)+; 1H NMR (CDCl3) δ 8.27-8.22 (m, 2H), 8.00 (dd, 1H), 7.41-7.34 (m, 3H), 7.23-7.18 (m, 1H), 3.72 (s, 3H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 1:10 ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-eba5564ff91749a7a04dedf78fcc2c06
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07211595B2

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