Isopropyltriphenylphosphonium iodide → 4-Bromo-2-methyl-1-(2-methylprop-1-en-1-yl)benzene

Reaction equation

[I-].[CH:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([CH3:4])[CH3:3].CC(C)([O-])C.[K+].[Br:30][C:31]1[CH:38]=[CH:37][C:34]([CH:35]=O)=[C:33]([CH3:39])[CH:32]=1>>[Br:30][C:31]1[CH:38]=[CH:37][C:34]([CH:35]=[C:2]([CH3:4])[CH3:3])=[C:33]([CH3:39])[CH:32]=1

Participants

Reactant 3

HCID 2723783Isopropyltriphenylphosphonium iodide

HCID 135551504-Bromo-2-methylbenzaldehyde

HCID 23665647Potassium tert-butoxide

Product 1

HCID 685247294-Bromo-2-methyl-1-(2-methylprop-1-en-1-yl)benzene

Procedure

The crude product of the title compound was synthesized by conducting the similar reaction to that mentioned in Example 23 (23d) using isopropyltriphenylphosphonium iodide (7.2 g, 17 mmol), potassium t-butoxide (2.0 g, 18 mmol), and 4-bromo-2-methylbenzaldehyde (2.4 g, 12 mmol) that was obtained in Example 27 (27b). Subsequently, the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (0:10 to 6:94) as the eluent to afford the title compound (2.2 g) in a yield of 84% as a colourless oily product.