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

HRID 1454080

Reaction equation

HRID 1454080 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 moles) and triphenylphosphine (924.4 g, 3.52 moles) in toluene (950 mL) was stirred at reflux for 12 hours. 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 about 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 hours
  2. customThe solid product precipitated from the reaction mixture throughout the course of the reaction
  3. temperaturecooled to about 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-97ed5e42eff14898b0af20e9c961caa6
Source dataset
uspto-grants-2009_01
Patent number
US07476762B2

Linked notes

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