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

HRID 36347

Reaction equation

HRID 36347 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 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##

Workup

  1. customReaction Scheme 6

Sources & evidence

ORD record
ord-8457dbac71164e0e899bdda678a44f59
Source dataset
uspto-grants-1995_05
Patent number
US05414007

Linked notes

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