Hydrazine → 4-(4-Methylpentyl)bromobenzene

HRID 36346

Reaktionsgleichung

Reaktionsgleichung von HRID 36346
O=[C:2]([C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1)[CH2:3][CH2:4][CH:5]([CH3:7])[CH3:6].[OH-].[K+].NN>>[CH3:6][CH:5]([CH3:7])[CH2:4][CH2:3][CH2:2][C:8]1[CH:9]=[CH:10][C:11]([Br:14])=[CH:12][CH:13]=1

Komponenten

4

Edukt 3

HCID 9321HydrazineHCID 14797Potassium HydroxideHCID 224090794-(1-Oxo-4-methyl-pentyl) bromobenzene

Produkt 1

HCID 224090934-(4-Methylpentyl)bromobenzene

Versuchsvorschrift

Reaction Scheme 5 discloses a specific synthetic route to 4-(4-methylpentyl)-phenylethyne (Compound 26). In accordance with this scheme, bromobenzene (Compound 27) is reacted under Friedel Crafts conditions (AlCl3) with the acid chloride (Compound 28) prepared in situ from 4-methyl valeric acid, to yield 4-(1-oxo-4-methyl-pentyl)bromobenzene (Compound 29). Compound 29 is reduced under Wolff-Kishner conditions (KOH, NH2NH2) to yield 4-(4-methylpentyl)bromobenzene (Compound 30). The bromobenzene derivative 30 is converted to the ethyne derivative 26 through the intermediate trimethylsilyl ethyne derivative 31 in a manner similar to the conversion described in connection with Reaction Scheme 3. ##STR9##

Quellen und Nachweise

ORD-Eintrag
ord-7ebbaf0fce9f41a09379d4b0a8659cb4
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05414007

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