Water → 3'-Ethoxy-4'-Methoxybiphenyl-3-Carboxylic Acid

HRID 448448Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448448
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4]N=1.[CH2:11]([O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH3:12].[C:25]([O-])([O-])=O.[Na+].[Na+].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:11]([O:13][C:14]1[CH:15]=[C:16]([C:25]2[CH:2]=[CH:10][CH:9]=[C:5]([C:6]([OH:8])=[O:7])[CH:4]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH3:12]

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2389326-Bromonicotinic acidHCID 46738762(3-Ethoxy-4-methoxyphenyl)boronic acid

Produkt 1

HCID 583071913'-Ethoxy-4'-Methoxybiphenyl-3-Carboxylic AcidAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

6-Bromonicotinic acid (2.02 g, 10.0 mmol) was dissolved in DME (80 mL) under nitrogen. Pd(PPh3)4 (0.58 g, 0.5 mmol) was added, and the resulting mixture was stirred at ambient temperature for 15 minutes. 3-ethoxy-4-methoxyphenylboronic acid (2.4 g, 12.2 mmol) and 2N Na2CO3 (40 mL, 80 mmol) were added, and the resulting mixture was heated to reflux with stirring for 24 hours. The mixture was poured into 300 mL of water and extracted with ethyl acetate (3×200 mL), and the product precipitated upon standing, providing 2.05 g of the product in 76% yield: 1H NMR (CDCl3) δ 1.53 (t, J=7.0 Hz, 3H), 3.96 (s, 3H), 4.22 (q, J=7.0 Hz, 2H), 7.00 (d, J=8.6 Hz, 1H), 7.53-7.58 (m, 2H), 7.91-8.02 (m, 2H), 8.12 (dd, J=6.9 Hz, J=1.5 Hz, 1H).

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux
  3. stirringwith stirring for 24 hours
  4. extractionextracted with ethyl acetate (3×200 mL)
  5. customthe product precipitated

Quellen und Nachweise

ORD-Eintrag
ord-b775f6c250fb4a8d8703bc841047ada8
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481568B2

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