Pyridine → 2-(4-(4-Chloro-3-fluorophenoxy)-3-fluorophenyl)ethanol

HRID 920347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 920347
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:4][C:3]=1[OH:11].[Cl:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][C:14]=1[F:22].N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([O:11][C:3]2[CH:4]=[CH:5][C:6]([CH2:8][CH2:9][OH:10])=[CH:7][C:2]=2[F:1])=[CH:15][C:14]=1[F:22]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 27786564-Chloro-3-fluorophenylboronic AcidHCID 451190812-Fluoro-4-(2-hydroxyethyl)phenol

Produkt 1

HCID 712365732-(4-(4-Chloro-3-fluorophenoxy)-3-fluorophenyl)ethanolAusbeute 21,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-fluoro-4-(2-hydroxyethyl)phenol (22.41 mmol, 3.5 g) and (4-chloro-3-fluorophenyl)boronic acid (45 mmol, 7.82 g) in dry CH2Cl2 (150 mL) were added copper (II) acetate (4.5 mmol 0.81 g), pyridine (45 mmol, 3.55 g), and 4 A molecular sieves in turn. The mixture was stirred at room temperature under N2 for 72 hours. The reaction mixture was filtered and the filtrate was concentrated to give crude product. The crude product was purified by silica gel chromatography to provide the desired product (1.4 g, 20%).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give crude product
  4. customThe crude product was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-740991e7e26a404a925ae4e8d108efa7
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273054B2

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