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

HRID 1590416

Reaction equation

HRID 1590416 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Reaction Scheme 6 discloses specific synthetic steps leading to 4-(1,1,4-trimethylpentyl)phenylethyne (Compound 34). In this synthetic route 4-(1-oxo-4-methyl-pentyl) bromobenzene (Compound 31, obtained for example as shown in Reaction Scheme 5) is reacted under a protective nitrogen atmosphere with trimethylaluminum in hexane to yield 4-(1,1,4-trimethyl-pentyl)bromobenzene (Compound 35). The bromobenzene derivative 35 is converted through the corresponding trimethylsilylethyne derivative 36 into the target intermediate 34 by treatment with trimethylsilyl ethyne and subsequently with KOH in isopropanol, as described above. ##STR10##

Workup

  1. customReaction Scheme 6

Sources & evidence

ORD record
ord-dd1c397b01ec49dd9c16149a92b91ea6
Source dataset
uspto-grants-1993_04
Patent number
US05202471

Linked notes

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