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

HRID 2247755Notes

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]([Cl: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]([Cl:39])[CH:32]=1

Participants

Reactant 3

HCID 2723783Isopropyltriphenylphosphonium iodide

HCID 141091094-Bromo-2-chlorobenzaldehyde

HCID 23665647Potassium tert-butoxide

Product 1

HCID 685242784-Bromo-2-chloro-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 (5.4 g, 12.6 mmol), potassium t-butoxide (1.5 g, 13.5 mmol) and 4-bromo-2-chlorobenzaldehyde (2.0 g, 9.0 mmol) that was obtained in Example 24 (24f). 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 (2.1 g) in a yield of 94% as a colourless oily product.

Workup

customthe similar reaction to

Sources & evidence

ORD record: ord-f4534d704a8c41049bf2aedb6decd25b
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687491B2

Reaction notes

Loading…