Triphenylphosphine → [2-(3,4-Difluorophenyl)-5-pyridyl]methyltriphenylphosphonium chloride

HRID 486367Notes

Reaction equation

HRID 486367 reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([F:16])[CH:10]=2)=[N:7][CH:8]=1.[C:17]1([P:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C(C)=CC=CC=1>[Cl-:1].[F:16][C:11]1[CH:10]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([CH2:2][P+:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:8][N:7]=2)[CH:14]=[CH:13][C:12]=1[F:15]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 190949555-Chloromethyl-2-(3,4-difluorophenyl)pyridine

Product 1

HCID 19094917[2-(3,4-Difluorophenyl)-5-pyridyl]methyltriphenylphosphonium chlorideYield 49.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 0.46 g of 5-chloromethyl-2-(3,4-difluorophenyl)pyridine, 0.6 g of triphenylphosphine and 10 ml of xylene was heated to boiling for 24 hours. After cooling the precipitate was filtered off, washed with toluene and dried. There was obtained 0.48 g of colourless [2-(3,4-difluorophenyl)-5-pyridyl]methyltriphenylphosphonium chloride, m.p. 259°-260.5° C.

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling the precipitate
  3. filtrationwas filtered off
  4. washwashed with toluene
  5. customdried

Sources & evidence

ORD record
ord-da089c1d69a748ea842b0f1fed25e78b
Source dataset
uspto-grants-1994_03
Patent number
US05292452

Reaction notes

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