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

HRID 2247769Notes

Reaction equation

HRID 2247769 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

4

Reactant 3

HCID 2723783Isopropyltriphenylphosphonium iodideHCID 135551504-Bromo-2-methylbenzaldehydeHCID 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.

Workup

  1. customthe similar reaction to

Sources & evidence

ORD record
ord-962653be1ae44e2ba1358c987d00f498
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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