Triphenylphosphine → (3-isopropoxycarbonylpropyl)triphenylphosphonium Bromide

HRID 2182831Notes

Reaction equation

[Br:1][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH:8]([CH3:10])[CH3:9])=[O:6].[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[Br-:1].[CH:8]([O:7][C:5]([CH2:4][CH2:3][CH2:2][P+:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:6])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 40 °C

Procedure

Isopropyl 4-bromobutyrate (16.0 g, 76.5 mmol) and triphenylphosphine (20.0 g, 76.5 mmol) in toluene (160 ml) were heated at reflux under nitrogen for 39 h. The mixture was allowed to cool (to approx 40° C.), filtered and the solid was washed with toluene (3 ×25 ml). The product was dried under vacuum to give a white solid (20.7 g, 57%); m.p. 198° C. (onset by DSC); 1H NMR (200 MHz, CDCl3) δ ppm 7.85-7.60 (15 H, m), 4.89 (1 H, heptet, J 6), 3.96-3.70 (2 H, m), 2.75 (2 H, t, J 6), 1.95-1.75 (2 H, m) and 1.13 (6 H, d, J 6).

Workup

temperatureat reflux under nitrogen for 39 h
filtrationfiltered
washthe solid was washed with toluene (3 ×25 ml)
customThe product was dried under vacuum

Sources & evidence

ORD record: ord-6ee1c47d33db498ead3e256ef92b77bd
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06897324B2

Reaction notes

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