Triphenylphosphine → (3-(1,3-Dioxoisoindolin-2-yl)propyl)triphenylphosphonium bromide

HRID 1021388

Reaction equation

HRID 1021388 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].[C:16]1([P:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[Br-:1].[O:15]=[C:6]1[C:7]2[C:8](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:10])[N:5]1[CH2:4][CH2:3][CH2:2][P+:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 21611N-3-Bromopropylphthalimide

Product 1

HCID 22018487(3-(1,3-Dioxoisoindolin-2-yl)propyl)triphenylphosphonium bromideYield 36.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N-(3-bromopropyl)phthalimide (25.0 g, 93.2 mmol) and triphenylphosphine (24.5 g, 93.2 mmol) in toluene (200 mL) was stirred and heated to reflux for 15 hours. The reaction mixture was cooled to ambient temperature and the resulting precipitate was collected by filtration, washed with toluene, and dried under vacuum to afford (3-(1,3-dioxoisoindolin-2-yl)propyl)triphenylphosphonium bromide as a white powder (17.9 g, 36% yield).

Workup

  1. temperatureheated
  2. temperatureto reflux for 15 hours
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with toluene
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ed1f28386bfe44bfaa095c331440ff0a
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Linked notes

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