Sodium Carbonate → 3'-Methoxy-biphenyl-3-carboxylic acid

HRID 377310

Reaktionsgleichung

Reaktionsgleichung von HRID 377310
C(=O)([O-])[O-].[Na+].[Na+].OB(O)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1.I[C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([OH:24])=[O:23]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:16][O:15][C:11]1[CH:10]=[C:9]([C:19]2[CH:27]=[CH:26][CH:25]=[C:21]([C:22]([OH:24])=[O:23])[CH:20]=2)[CH:14]=[CH:13][CH:12]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 120603-Iodobenzoic acidHCID 2734370(3-Methoxyphenyl)boronic acid

Produkt 1

HCID 27595503'-Methoxy-biphenyl-3-carboxylic acidAusbeute 54,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium carbonate (11.13 g) was added portionwise to a stirred solution of dihydroxy-(3-methoxyphenyl)borane (5.85 g) and 3-iodobenzoic acid (8.68 g) in water (138 ml) at room temperature, and then palladium(II) acetate (78.6 mg) was added portionwise thereto at the same temperature. The resulting mixture was stirred at the same temperature for 4 hours. The reaction mixture was filtered, then the filtrate was washed twice with diethyl ether and adjusted to pH 2.0 with 6N hydrochloric acid. The precipitated powder was collected by filtration and dissolved in ethyl acetate. The solution was dried over magnesium sulfate and evaporated in vacuo. The residue was washed with n-hexane to afford 3'-methoxy-3-biphenylcarboxylic acid (4.34 g) as a powder.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate was washed twice with diethyl ether
  3. filtrationThe precipitated powder was collected by filtration
  4. dissolutiondissolved in ethyl acetate
  5. dry with materialThe solution was dried over magnesium sulfate
  6. customevaporated in vacuo
  7. washThe residue was washed with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-6e67c1fef478470f8d6029e0173f055c
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06025375

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