Toluene → 2-[4-(Pyrrolidin-1-yl)phenyl]acetic acid

HRID 2251911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251911
C1(C)C=CC=CC=1.CC(C)([O-])C.[Na+].Br[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([OH:24])=[O:23])=[CH:17][CH:16]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[N:25]1([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([OH:24])=[O:23])=[CH:17][CH:16]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 31268PyrrolidineHCID 74654Benzeneacetic acid, 4-bromo-HCID 23676156Sodium t-butoxide

Produkt 1

HCID 141545872-[4-(Pyrrolidin-1-yl)phenyl]acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Toluene (10 ml) was added to a mixture of palladium acetate (22.3 mg, 0.10 mmol), 2-(biphenyl)-di-tert-butylphosphine (59.8 mg, 0.20 mmol) and sodium tert-butoxide (2.40 g, 25.0 mmol), and then (4-bromophenyl)acetic acid (2.15 g, 10.0 mmol) and pyrrolidine (1.10 ml, 13.2 mmol) were added thereto. The obtained mixture was heated at 70° C. for 46 hours. Water (20 ml) was added to the reaction mixture. pH of the aqueous layer was controlled at 2 or below. The aqueous layer was washed with toluene and adjusted to pH 4 to 5. After stirring the reaction mixture in ice-bath for a while, it was filtered to obtain the title compound in the form of a light yellow solid (1.1 g, 54%).

Aufarbeitung

  1. washThe aqueous layer was washed with toluene
  2. filtrationwas filtered

Quellen und Nachweise

ORD-Eintrag
ord-ba8ad723f05e4b14a59f94732b403121
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07320973B2

Notizen zur Reaktion

Wird geladen…