Triphenylphosphine → HCID 10505810, compound

HRID 260003Notes

Reaction equation

HRID 260003 reaction equation
[Br:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]([F:11])([F:10])[F:9])[C:3]1=[O:12].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[Br-:1].[O:12]=[C:3]1[CH:2]([P+:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:6][CH2:5][N:4]1[CH2:7][C:8]([F:11])([F:10])[F:9]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 10586483HCID 10586483, compound

Product 1

HCID 10505810HCID 10505810, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
5 °C

Procedure

189 g (0.77 Mol) rac-3-Bromo-1-(2,2,2-trifluoroethyl)-2-pyrrolidone were dissolved in 1 l toluene, and 222 g (0.85 Mol) triphenylphosphine were added. The mixture was refluxed over-night in an argon atmosphere, the product starting to precipitate. The mixture was then cooled to 5° C. and the slightly brownish crystals were filtered off. They were stirred twice in 1 l THF, filtered and dried in a vacuum at 50° C. Yield: 308 g (79%) colorless crystals 1H-NMR (3): δ[ppm]2.17 (m, 1 H); 3.2-3.5 (m, 3 H); 3.93 (dd, 1H); 4.24 m, 1H); 6.91 (m, 1H); 7.60-8.03 (arom., m, 15H). IR (KBr): 1690 cm-1 MS(ISP): 428.3 (M+)

Workup

  1. temperatureThe mixture was refluxed over-night in an argon atmosphere
  2. customto precipitate
  3. filtrationthe slightly brownish crystals were filtered off
  4. filtrationfiltered
  5. customdried in a vacuum at 50° C

Sources & evidence

ORD record
ord-b3f020462643425a9febf039a354afe8
Source dataset
uspto-grants-1996_06
Patent number
US05523400

Reaction notes

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