Triphenylphosphonium bromide → 2-(1-Methyl-2-oxo-propyloxy)-5-iodobenzyltriphenylphosphonium bromide

HRID 2399308Notes

Reaction equation

O[CH2:2][C:3]1[CH:15]=[C:14]([I:16])[CH:13]=[CH:12][C:4]=1[O:5][C:6]([CH3:11])(C)[C:7](=[O:9])[CH3:8].[BrH:17].[C:18]1([P:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C>[Br-:17].[CH3:11][CH:6]([O:5][C:4]1[CH:12]=[CH:13][C:14]([I:16])=[CH:15][C:3]=1[CH2:2][P+:24]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:7](=[O:9])[CH3:8]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture containing crude 3-(2-hydroxymethyl-4-iodophenoxy)-3-methyl-2-butanone (0.84 g, 0.00252 mol) and triphenylphosphine hydrobromide (0.86 g, 0.00252 mol) in acetonitrile (5 ml) was heated at 90° C. for 2.5 hours. After evaporation of the solvent, the crude solid product was washed with ether and dissolved in ethanol (3 ml). Hot isopropyl ether (8 ml) was added until a light precipitate formed, and the solution was left at room temperature overnight. The crystalline product was recovered by filtration to yield 0.77 g (50%) of 2-(1-methyl-2-oxo-propyloxy)-5-iodobenzyltriphenylphosphonium bromide, m.p. 230° C.

Workup

customAfter evaporation of the solvent
washthe crude solid product was washed with ether
dissolutiondissolved in ethanol (3 ml)
additionHot isopropyl ether (8 ml) was added until a light precipitate
customformed
filtrationThe crystalline product was recovered by filtration

Sources & evidence

ORD record: ord-e5fb555c28fa4706a72430c42b5ab841
Source dataset: uspto-grants-1995_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05447943

Reaction notes

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