Triphenylphosphine → (3-Cyanopropyl)triphenylphosphonium bromide

HRID 348746

Reaction equation

HRID 348746 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][CH2:22][CH2:23][C:24]#[N:25]>C1(C)C=CC=CC=1>[Br-:20].[C:24]([CH2:23][CH2:22][CH2:21][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)#[N:25]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 214124-Bromobutyronitrile

Product 1

HCID 3036619(3-Cyanopropyl)triphenylphosphonium bromideYield 50.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triphenylphosphine (1.4789 g) was dissolved in anhydrous toluene (44.4 ml) and then added with 4-bromo-butyronitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (834.7 mg), followed by thermal reflux for 22 hours. After the reaction, a precipitated product was filtrated. The precipitate obtained through filtration was washed with toluene and thermally dried under reduced pressure, thereby obtaining the subject compound (1.1697 g) as a white solid.

Workup

  1. temperatureby thermal reflux for 22 hours
  2. customAfter the reaction
  3. filtrationa precipitated product was filtrated
  4. customThe precipitate obtained through filtration
  5. washwas washed with toluene
  6. customthermally dried under reduced pressure

Sources & evidence

ORD record
ord-d7a84e5bd46549759e2c17077a7be90a
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Linked notes

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