Triphenylphosphine → HCID 23315145, compound

HRID 745250Notes

Reaction equation

HRID 745250 reaction equation
[C:1]1(=[O:20])[N:5]([CH2:6][C:7]2[CH:14]=[CH:13][C:10]([CH2:11][Br:12])=[CH:9][CH:8]=2)[C:4](=[O:15])[C:3]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:2]12.[C:21]1([P:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1C=CC=CC=1>[Br-:12].[C:1]1(=[O:20])[N:5]([CH2:6][C:7]2[CH:14]=[CH:13][C:10]([CH2:11][P+:27]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:9][CH:8]=2)[C:4](=[O:15])[C:3]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:2]12

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 10496630HCID 10496630, compound

Product 1

HCID 23315145HCID 23315145, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 29.2 g of 4-phthalimidomethylbenzyl bromide, were added 400 ml of benzene and 23.2 g of triphenylphosphine. The mixture was heated under reflux for 2 hours. The reaction mixture was cooled in ice. The crystals precipitated out of the reaction mixture were collected by filtration and washed thoroughly with benzene to yield 35.5 g of 4-phthalimidomethylbenzyltriphenylphosphonium bromide; m.p. 245°-246° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe reaction mixture was cooled in ice
  4. customThe crystals precipitated out of the reaction mixture
  5. filtrationwere collected by filtration
  6. washwashed thoroughly with benzene

Sources & evidence

ORD record
ord-0c5ab0a8dd244ad395ca984625683058
Source dataset
uspto-grants-1986_07
Patent number
US04598077

Reaction notes

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