1,1,1-Trifluoro-2-iodoethane → Diphenyl(2,2,2-trifluoroethyl)phosphine oxide

HRID 2260901Notes

Reaction equation

HRID 2260901 reaction equation
[C:1]1([P:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:8]CC)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:17][C:18]([F:22])([F:21])[CH2:19]I>>[F:17][C:18]([F:22])([F:21])[CH2:19][P:7](=[O:8])([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 677091,1,1-Trifluoro-2-iodoethaneHCID 69754Ethyl diphenylphosphinite

Product 1

HCID 11323568Diphenyl(2,2,2-trifluoroethyl)phosphine oxideYield 51%

Procedure

Ethyl diphenylphosphinite (b1; 20.0 g) and 1,1,1-trifluoro-2-iodoethane (b2; 36.5 g) were put into a reaction vessel under an argon atmosphere, and stirred at room temperature for 4 days. The resulting mixture was purified by means of fraction-collecting column chromatography using ethyl acetate as the eluent and silica gel as the stationary phase powder, and further purified by recrystallization from a mixed solvent of toluene and heptane (volume ratio of toluene:heptane=1:1), and then dried, whereby 12.6 g of 2,2,2-trifluoroethyl diphenylphosphine oxide (b3) was obtained. The yield based on the compound (b1) was 51.2%.

Workup

  1. customThe resulting mixture was purified by means
  2. customof fraction-collecting column chromatography
  3. customfurther purified by recrystallization from a mixed solvent of toluene and heptane (volume ratio of toluene:heptane=1:1)
  4. customdried

Sources & evidence

ORD record
ord-93ec32f1bdfe4060aa5a89d1c5a72512
Source dataset
uspto-grants-2010_12
Patent number
US07846514B2

Reaction notes

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