Ethyl Acrylate → HCID 90442064, Verbindung

HRID 2177312

Reaktionsgleichung

Reaktionsgleichung von HRID 2177312
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[CH:14]=[CH2:15].CCN(C(C)C)C(C)C>Cl[Pd]Cl.CN(C)C=O>[OH:8][C:5]1[CH:6]=[CH:7][C:2](/[CH:15]=[CH:14]/[C:13]([O:17][CH2:18][CH3:19])=[O:16])=[C:3]([C:9]([F:12])([F:11])[F:10])[CH:4]=1

Komponenten

6

Edukt 3

HCID 8821Ethyl AcrylateHCID 81531DiisopropylethylamineHCID 222773074-Bromo-3-(trifluoromethyl)phenol

Produkt 1

HCID 90442064HCID 90442064, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24290Palladium ChlorideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Into a 500-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 4-bromo-3-(trifluoromethyl)phenol (5 g, 20.75 mmol, 1.00 equiv), N,N-dimethylformamide (60 mL), ethyl prop-2-enoate (10.5 g, 104.88 mmol, 5.06 equiv), PdCl2 (370 mg, 2.09 mmol, 0.10 equiv), P(tolyl)3 (1.28 g, 4.21 mmol, 0.20 equiv), DIEA (16.25 g). The resulting solution was stirred for overnight at 90° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/8). This resulted in 2.6 g (42%) of ethyl (2E)-3-[4-hydroxy-2-(trifluoromethyl)phenyl]prop-2-enoate as a light yellow solid.

Aufarbeitung

  1. customInto a 500-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customThis resulted in 2.6 g (42%) of ethyl (2E)-3-[4-hydroxy-2-(trifluoromethyl)phenyl]prop-2-enoate as a light yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-40226ac7e7a3447c9b9553d7579d2e6e
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067898B1

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