Triphenylphosphine → Triphenyl(3,3,3-trifluoropropyl)phosphanium iodide

HRID 1987569Notes

Reaction equation

HRID 1987569 reaction equation
[F:1][C:2]([F:7])([F:6])[CH2:3][CH2:4][I:5].[C:8]1([P:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1(C)C=CC=CC=1>[I-:5].[F:1][C:2]([F:7])([F:6])[CH2:3][CH2:4][P+:14]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 1561651,1,1-Trifluoro-3-iodopropane

Product 1

HCID 19694095Triphenyl(3,3,3-trifluoropropyl)phosphanium iodideYield 92.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1,1,1-trifluoro-3-iodopropane (263.1 g, 1.17 mol) and triphenylphosphine (924.4 g, 3.52 mol) in toluene (950 mL) was stirred at reflux for 12 h. The solid product precipitated from the reaction mixture throughout the course of the reaction. The reaction was allowed to cool to ambient temperature and then cooled to ˜5° C. in an ice bath. The solid precipitate was isolated by filtration and dried in vacuo at 25° C. to give a white powder (526.5 g, 92%).

Workup

  1. temperatureat reflux for 12 h
  2. customThe solid product precipitated from the reaction mixture throughout the course of the reaction
  3. temperaturecooled to ˜5° C. in an ice bath
  4. customThe solid precipitate was isolated by filtration
  5. customdried in vacuo at 25° C.

Sources & evidence

ORD record
ord-d6c4706e931b49e4b31cd5677a442b66
Source dataset
uspto-grants-2009_06
Patent number
US07550629B2

Reaction notes

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