Triethylamine → 3-(4-Hydroxy-3-fluorophenyl)-acrylic acid ethyl ester

HRID 1387460

Reaktionsgleichung

Reaktionsgleichung von HRID 1387460
[F:1][C:2]1[CH:7]=[C:6](Br)[CH:5]=[CH:4][C:3]=1[OH:9].[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH2:12].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>ClCCl.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:15]([O:14][C:10](=[O:13])[CH:11]=[CH:12][C:6]1[CH:5]=[CH:4][C:3]([OH:9])=[C:2]([F:1])[CH:7]=1)[CH3:16]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 27249814-Bromo-2-fluorophenol

Produkt 1

HCID 540331993-(4-Hydroxy-3-fluorophenyl)-acrylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2-fluoro-4-bromophenol 15-1 (50 g, 261.8 mmol), ethyl acrylate (34 mL), Pd(OAc)2 (2.5 g), tri-o-tolylphosphine (5 g) and triethylamine (83 mL) was heated to 100° C. in a sealed tube for 12 h. The reaction was cooled to room temperature and diluted with dichloromethane (100 mL). The organic solution was washed with 10% aq. citric acid (40 mL), satd aq NaHCO3, and brine (40 mL). The organic solution was dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (50:50 hexanes/EtOAc to 100% EtOAc) to give acrylic acid 15-2 as a white solid.

Aufarbeitung

  1. washThe organic solution was washed with 10% aq. citric acid (40 mL)
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (50:50 hexanes/EtOAc to 100% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-47159f5c701f413e828b5d6c48b65e1e
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06268378B1

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