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

HRID 439918

Reaction equation

HRID 439918 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-d438310c2e714b6db37addab874fe9fe
Source dataset
uspto-grants-1996_05
Patent number
US05516904

Linked notes

Loading…