Triphenylphosphine → Triphenyl[(pyridin-4-yl)methyl]phosphanium chloride--hydrogen chloride (1/1/1)

HRID 2390869Notes

Reaction equation

HRID 2390869 reaction equation
[ClH:1].[Cl:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.[CH:10]1[CH:15]=[CH:14][C:13]([P:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1>CC#N.C1(C)C=CC=CC=1>[ClH:2].[Cl-:1].[C:23]1([P+:16]([C:13]2[CH:12]=[CH:11][CH:10]=[CH:15][CH:14]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:3][C:4]2[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 745704-(Chloromethyl)pyridinium chloride

Product 1

HCID 21255469Triphenyl[(pyridin-4-yl)methyl]phosphanium chloride--hydrogen chloride (1/1/1)Yield 94%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

step 1—To a suspension of 4-chloromethyl-pyridine hydrochloride (2.72 g, 16.6 mmol) in MeCN (20 mL) was added PPh3 (4.57 g, 17.4 mmol). The mixture was warmed to reflux. After 18 h the mixture was cooled taken up in 20 mL toluene and filtered. The collected solid was washed with toluene and dried in vacuum to afford triphenyl(4-pyridylmethyl)phosphonium chloride hydrochloride (6.61 g, 94%) as a white solid.

Workup

  1. temperatureThe mixture was warmed to reflux
  2. temperatureAfter 18 h the mixture was cooled
  3. filtrationfiltered
  4. washThe collected solid was washed with toluene
  5. customdried in vacuum

Sources & evidence

ORD record
ord-b948d3b0737f4e4a8b60ed53e79def81
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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