Nitrilooxonium tetrafluoroborate → Ethyl 6-fluoro-2-naphthoate

HRID 1270765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1270765
[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11](N)[CH:12]=2)[CH:7]=1)=[O:5])[CH3:2].[F:17][B-](F)(F)F.N#[O+]>ClC1C=CC=CC=1Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:17])[CH:12]=2)[CH:7]=1)=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 11137142Nitrilooxonium tetrafluoroborateHCID 58111738Ethyl 6-amino-2-naphthoate

Produkt 1

HCID 68806046Ethyl 6-fluoro-2-naphthoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 72391,2-DichlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 6-amino-2-naphthoic acid ethyl ester (500 mg, 2.32 mmol) and nitrosonium tetrafluoroborate (298 mg, 2.56 mmol) in 1,2-dichlorobenzene (10 mL) is stirred at room temperature for 12 hours and at 110° C. for 1 hour. After cooling to room temperature, the reaction mixture is concentrated by rotary evaporator under high vacuum. The residual oil is purified by flash chromatography on silica gel (dichloromethane) to give 6-fluoro-2-naphthoic acid ethyl ester as a yellow oil.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture is concentrated by rotary evaporator under high vacuum
  3. customThe residual oil is purified by flash chromatography on silica gel (dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-732148d7e05b49deb86913714cf1d169
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202364B2

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