Ethyl Acrylate → 3-(4-Fluoro-2-methyl-phenyl)-acrylic acid ethyl ester

HRID 1822340

Reaktionsgleichung

Reaktionsgleichung von HRID 1822340
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH3:9].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CCN(C(C)C)C(C)C.[C:41]([O:45][CH2:46][CH3:47])(=[O:44])[CH:42]=[CH2:43]>C(#N)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:46]([O:45][C:41](=[O:44])[CH:42]=[CH:43][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH3:9])[CH3:47]

Komponenten

7

Edukt 4

HCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 967432-Bromo-5-fluorotoluene

Produkt 1

HCID 537177243-(4-Fluoro-2-methyl-phenyl)-acrylic acid ethyl esterAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 7854PropionitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 1-bromo-4-fluoro-2-methyl-benzene (5.00 g, 26.45 mmol), palladium acetate (0.59 g, 2.64 mmol), tri-o-tolylphosphine (1.61 g, 5.29 mmol), DIPEA (13.8 mL, 79.35 mmol) and ethyl acrylate (3.34 mL, 105.80 mmol) in propionitrile (106 mL) is stirred at 90° C. under nitrogen overnight. The mixture is ed off through Celite and washed with ethyl acetate. The mixture is concentrated under reduced pressure, purified by flash chromatography by eluting with hexane:ethyl acetate 10:1 to afford the title compound (5.50 g, 99%). Rf=0.49 (hexane:ethyl acetate 5:1). 1H NMR (300 MHz, CDCl3): δ1.33 (t, 3H, J=7.3 Hz), 2.41 (s, 3H), 4.26 (q, 2H, J=7.3 Hz), 6.28 (d, 1H, J=16.0 Hz), 6.88-6.91 (m, 2H), 7.48-7.53 (m, 1H), 7.88 (d, 1H, J=15.8 Hz).

Aufarbeitung

  1. washwashed with ethyl acetate
  2. concentrationThe mixture is concentrated under reduced pressure
  3. custompurified by flash chromatography
  4. washby eluting with hexane:ethyl acetate 10:1

Quellen und Nachweise

ORD-Eintrag
ord-ead20c207ab5410d87a9aae32b32fc4c
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608639B2

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