Methanol → 2-[3-Fluoro-4-hydroxy-phenyl]-cyclopropanecarboxylic acid ethyl ester

HRID 62889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 62889
[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([F:17])[CH:10]=1)=[O:5])[CH3:2].B(Br)(Br)Br.CO>C(Cl)Cl>[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([F:17])[CH:10]=1)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 25134Boron tribromideHCID 58566289Ethyl 2-(3-fluoro-4-methoxyphenyl)cyclopropanecarboxylate

Produkt 1

HCID 585667072-[3-Fluoro-4-hydroxy-phenyl]-cyclopropanecarboxylic acid ethyl esterAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

After 2-(3-fluoro-4-methoxy-phenyl)-cyclopropanecarboxylic acid ethyl ester (0.494 g, 2.07 mmol) obtained in Step B was dissolved in anhydrous DCM (7 mL), BBr3 1 M DCM solution (3 mL, 3.11 mmol) was added thereto at −78° C., and the mixture was stirred at room temperature for 3 hours. After the termination of the reaction, the reactant was added with MeOH, concentrated under reduced pressure, and purified by column chromatography (eluent, EtOAc/Hex=1/2) to obtain the title compound (0.424 g, 91%).

Aufarbeitung

  1. customAfter the termination of the reaction
  2. concentrationconcentrated under reduced pressure
  3. custompurified by column chromatography (eluent, EtOAc/Hex=1/2)

Quellen und Nachweise

ORD-Eintrag
ord-e91ce22eda65405f81aff1bdb27a793d
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447044B2

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