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

HRID 2226707Notes

Reaction equation

HRID 2226707 reaction equation
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]

Participants

5

Reactant 4

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

Product 1

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

Procedure

Reaction Scheme 5 discloses a specific synthetic route to 4-(4-methylpentyl)-phenylethyne (Compound 28). In accordance with this scheme, bromobenzene (Compound 29) is reacted under Friedel Crafts conditions (AlCl3) with the acid chloride (Compound 30) prepared in situ from 4-methyl valeric acid, to yield 4-(1-oxo-4-methyl-pentyl) bromobenzene (Compound 31). Compound 31 is reduced under Wolff-Kishner conditions (KOH, NH2NH2) to yield 4-(4-methylpentyl) bromobenzene (Compound 32). The bromobenzene derivative 32 is converted to the ethyne derivative 28 through the intermediate trimethylsilyl ethyne derivative 33 in a manner similar to the conversion described in connection with Reaction Scheme 3. ##STR9##

Workup

  1. customReaction Scheme 5

Sources & evidence

ORD record
ord-965d261fc8f24cdbafb3aff121cad060
Source dataset
uspto-grants-1994_09
Patent number
US05349105

Reaction notes

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