Hydrochloric Acid → 4-(n-Pentoxyphenyl)-4'-carboxybiphenyl

HRID 264599

Reaktionsgleichung

Reaktionsgleichung von HRID 264599
C(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)CCCC.I[C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=1.[C:32](=[O:35])([O-])[O-].[Na+].[Na+].Cl>C(O)C.C1(C)C=CC=CC=1.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>[CH2:32]([O:35][C:18]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:10]1[CH:9]=[CH:8][C:7]([C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=2)=[CH:12][CH:11]=1)[CH2:12][CH2:7][CH2:8][CH3:9]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 120854-Iodobenzoic acidHCID 113580714'-Pentyloxybiphenyl-4-boronic Acid

Produkt 1

HCID 214795504-(n-Pentoxyphenyl)-4'-carboxybiphenylAusbeute 70,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirred mixture of 4-(4-n-pentoxyphenyl)phenylboronic acid (1.0 g, 3.52 mmol) and 4-iodobenzoic acid (874 mg, 3.52 mmol) in ethanol (11 ml) and toluene (30 ml) was added an aqueous solution of sodium carbonate (2M, 5.3 ml, 10.6 mmol) followed by tetrakis(triphenylphosphine)palladium (204 mg, 5 mol %). The reaction mixture was heated at 100° C. under a nitrogen atmosphere for a period of 18 h. The cooled mixture was acidified to pH 3 (1N HCl) and partitioned between ethyl acetate and water. The organic phase was washed with water (3×) and brine, dried with magnesium sulfate, and filtered through a bed of Celite. The solvent was removed in vacuo to give crude product which was purified by flash silica gel chromatography to provide 4-(n-pentoxyphenyl)-4'-carboxybiphenyl (450 mg): 1H NMR (400 MHz, DMSO-d6) δ0.89 (t, 3H), 1.37 (m, 4H), 1.72 (m, 2H), 3.98 (t, 2H), 7.01 (d, 2H).

Aufarbeitung

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed with water (3×) and brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered through a bed of Celite
  5. customThe solvent was removed in vacuo
  6. customto give crude product which
  7. customwas purified by flash silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0ab78d509caa495cabb27b4ae2337c97
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646245

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