Hydrazine → 4-(4-Methylpentyl)bromobenzene

HRID 2226708Notes

Reaction equation

HRID 2226708 reaction equation
O=[C:2]([C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1)[CH2:3][CH2:4][CH:5]([CH3:7])[CH3:6].[OH-].[K+].NN>>[CH3:6][CH:5]([CH3:7])[CH2:4][CH2:3][CH2:2][C:8]1[CH:9]=[CH:10][C:11]([Br:14])=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 9321HydrazineHCID 14797Potassium HydroxideHCID 224090794-(1-Oxo-4-methyl-pentyl) bromobenzene

Product 1

HCID 224090934-(4-Methylpentyl)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##

Sources & evidence

ORD record
ord-2f605a78644a402a862fa26dda77aeea
Source dataset
uspto-grants-1994_09
Patent number
US05349105

Reaction notes

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