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

HRID 854

Reaction equation

HRID 854 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.[F:20][C:21]([F:26])([F:25])[CH2:22][CH2:23][I:24]>>[I-:24].[F:20][C:21]([F:26])([F:25])[CH2:22][CH2:23][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

Participants

3

Reactant 2

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

Product 1

HCID 19694095Triphenyl(3,3,3-trifluoropropyl)phosphanium iodideYield 76.5%

Procedure

A solution of triphenylphosphine (Aldrich, 11.7 g) and 3,3,3-trifluoropropyl iodid (Lancaster, 10 g) was vigorously refluxed in xylenes (75 mL) for 2 days. The solid which formed was filtered and washed with xylenes then air dried to yield a white solid (16.6 g). 1H NMR and elemental analysis are consistent with the proposed structure.

Workup

  1. customThe solid which formed
  2. filtrationwas filtered
  3. washwashed with xylenes
  4. customair dried

Sources & evidence

ORD record
ord-05670d53f7f64813b11aec885e767cda
Source dataset
uspto-grants-1998_03
Patent number
US05723458

Linked notes

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