Nitric Acid → 4,5-Dimethoxy-2-nitrophenol

HRID 2262864

Reaktionsgleichung

Reaktionsgleichung von HRID 2262864
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N+:12]([O-])([OH:14])=[O:13]>CC(O)=O>[CH3:10][O:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([OH:11])=[C:6]([N+:12]([O-:14])=[O:13])[CH:7]=1

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 162513,4-Dimethoxyphenol

Produkt 1

HCID 2971214,5-Dimethoxy-2-nitrophenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

In SCHEME 9 3,4-dimethoxyphenol (36) is selectively nitrated with 70% HNO3 in AcOH to give 4,5-dimethoxy-2-nitrophenol (37) which is further converted to the corresponding triflate (38) with trifluoromethylsulfonic anhydride (Tf2O) and pyridine in dichloromethane. Triflate (38) is reacted under inert conditions with a boronic acid of general type (31) under Suzuki-type basic conditions (Pd(PPh3)4 and aqueous potassium phosphate in toluene) to a biaryl of type (39). Biaryl (39) is further hydrolized with aqueous lithium hydroxide in THF and MeOH or MeCN to give the corresponding carboxylic acid (40) which is converted to a building block of type (41) by reaction with oxalyl chloride in anhydrous dichloromethane.

Quellen und Nachweise

ORD-Eintrag
ord-470721f2c58e44d09b9fdde48812aa67
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851501B2

Verknüpfte Notizen

Wird geladen…