Benzyl Bromide → 3-(Benzyloxy)-4-methoxyaniline

HRID 19986

Reaktionsgleichung

Reaktionsgleichung von HRID 19986
[OH:1][C:2]1[CH:3]=[C:4]([N+:10]([O-])=O)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>CC(C)=O>[CH2:13]([O:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][CH3:9])[NH2:10])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 694712-Methoxy-5-nitrophenol

Produkt 1

HCID 125477223-(Benzyloxy)-4-methoxyaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

3-Hydroxy-4-methoxy-1-nitrobenzene was benzylated by refluxing with benzyl bromide with potassium carbonate as a base in acetone which on reduction with sodium dithionite gave 3-benzyloxy-4-methoxy aniline. 4-Hydroxy-3-methoxy benzoic acid was converted to its methyl ester by refluxing in methanol in presence of an acid. The hydroxyl was benzylated using benzyl bromide and potassium carbonate. The ester was hydrolyzed with sodium hydroxide to provide the acid. The aniline and acid were coupled using N,N-1,3-diisopropylcarbodiimide in presence of 1-hydroxybenzotriazole to provide the amide. Finally the benzyl group was removed by hydrogenation in presence of palladium on carbon.

Quellen und Nachweise

ORD-Eintrag
ord-8ef1cd813a7f4e91bce9880429a58b48
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745490B2

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