Morpholine → 4-(2-Fluoro-5-vinyl-phenyl)-morpholine

HRID 857022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857022
Br[C:2]1[CH:7]=[C:6]([CH:8]=[CH2:9])[CH:5]=[CH:4][C:3]=1[F:10].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C(Cl)Cl>[F:10][C:3]1[CH:4]=[CH:5][C:6]([CH:8]=[CH2:9])=[CH:7][C:2]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Komponenten

6

Edukt 3

HCID 8083MorpholineHCID 62657Potassium Phosphate, TribasicHCID 218646502-Bromo-4-ethenyl-1-fluorobenzene

Produkt 1

HCID 218646624-(2-Fluoro-5-vinyl-phenyl)-morpholine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of 2-bromo-1-fluoro-4-vinyl-benzene (8 g), morpholine (20 mL), Pd2(dba)2 (1.83 g), di-t-butyl-biphenylphosphine (1.2 g), K3PO4 (17 g) in DME (60 mL) was stirred at reflux for 4 h. The reaction mixture was cooled down to room temperature, diluted with methylene chloride, and filtered. The filtrate was concentrated in vacuo. The crude product was purified by Flash Chromatography of Biotage eluting with 7% ethyl acetate in hexanes to give the title compound as an oil (5 g).

Aufarbeitung

  1. temperatureat reflux for 4 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe crude product was purified by Flash Chromatography of Biotage
  5. washeluting with 7% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c1c202ded1fe4153844f931c9f6e8567
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144881B2

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