Bromobenzene → 4-(1-Oxo-4-methyl-pentyl) bromobenzene

HRID 36345

Reaktionsgleichung

Reaktionsgleichung von HRID 36345
CC(C)CCCC1C=CC(C#C)=CC=1.[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Al+3].[Cl-].[Cl-].[Cl-].[CH3:26][CH:27]([CH3:33])[CH2:28][CH2:29][C:30](O)=[O:31]>>[O:31]=[C:30]([C:19]1[CH:20]=[CH:21][C:16]([Br:15])=[CH:17][CH:18]=1)[CH2:29][CH2:28][CH:27]([CH3:33])[CH3:26]

Komponenten

5

Edukt 4

HCID 7961Bromobenzene2×HCID 12587Isocaproic acidHCID 6451240Aluminum(III) ChlorideHCID 153375604-(4-Methylpentyl)-phenylethyne2×

Produkt 1

HCID 224090794-(1-Oxo-4-methyl-pentyl) 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##

Aufarbeitung

  1. customReaction Scheme 5

Quellen und Nachweise

ORD-Eintrag
ord-f287d333fd274c6d841027fe31376c4c
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05414007

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