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

HRID 990111

Reaktionsgleichung

Reaktionsgleichung von HRID 990111
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:13]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 181694-Hydroxy-3-nitrobenzaldehyde

Produkt 1

HCID 70235544-(Benzyloxy)-3-nitrobenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Substituted benzyl bromide compounds can also be prepared from commercially available substituted benzaldehydes, benzoic acids and benzoic esters by first converting these compounds to the corresponding alcohol. Exemplary synthetic methodology to provide substituted benzyl bromide from benzyl aldehyde is described below. For example, as illustrated in Scheme 12, treatment of 4-hydroxy-3-nitro-benzaldehyde 73 with benzyl bromide in the presence of K2CO3 in DMF at 65° C. gives 4-benzyloxy-3-nitro-benzaldehyde 74. Reduction of compound 74 in methanol with NaBH4 affords the alcohol 75 and subsequent bromination using PBr3 in diethyl ether provides the desired bromide compound 76.

Quellen und Nachweise

ORD-Eintrag
ord-0eaa3129489645d48cc52af19fec94cd
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458829B1

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