4-(1,1,4-Trimethylpentyl)phenylethyne → 4-(1,1,4-Trimethylpentyl)bromobenzene

HRID 257981

Reaktionsgleichung

Reaktionsgleichung von HRID 257981
[CH3:1][C:2]([C:9]1[CH:14]=[CH:13][C:12](C#C)=[CH:11][CH:10]=1)([CH3:8])[CH2:3][CH2:4][CH:5]([CH3:7])[CH3:6].O=C(C1C=CC([Br:30])=CC=1)CCC(C)C.C[Al](C)C>CCCCCC>[CH3:1][C:2]([C:9]1[CH:14]=[CH:13][C:12]([Br:30])=[CH:11][CH:10]=1)([CH3:8])[CH2:3][CH2:4][CH:5]([CH3:7])[CH3:6]

Komponenten

5

Edukt 3

HCID 149896684-(1,1,4-Trimethylpentyl)phenylethyne2×HCID 16682925TrimethylaluminumHCID 224090794-(1-Oxo-4-methyl-pentyl) bromobenzene2×

Produkt 1

HCID 224090834-(1,1,4-Trimethylpentyl)bromobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Reaction Scheme 6 discloses specific synthetic steps leading to 4-(1,1,4-trimethylpentyl)phenylethyne (Compound 32). In this synthetic route 4-(1-oxo-4-methyl-pentyl) bromobenzene (Compound 29, obtained as shown in Reaction Scheme 5) is reacted under a nitrogen atmosphere with trimethylaluminum in hexane to yield 4-(1,1,4-trimethylpentyl)bromobenzene (Compound 33). The bromobenzene derivative 33 is converted through the corresponding trimethylsilylethyne derivative 34 into the target intermediate 32 by treatment with trimethylsilyl ethyne and subsequently with KOH in isopropanol, as described above. ##STR10##

Aufarbeitung

  1. customReaction Scheme 6

Quellen und Nachweise

ORD-Eintrag
ord-ebf2062b80fe42999a4257882c99b254
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05264456

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