Tributylphosphine → Tributyl((4-chlorophenylthio)methyl)phosphonium chloride

HRID 46407Notes

Reaction equation

HRID 46407 reaction equation
[CH2:1]([P:5]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][CH2:22]Cl)=[CH:17][CH:16]=1>O1CCOCC1.CCCCCC>[Cl-:14].[CH2:10]([P+:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:22][S:21][C:18]1[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=1)[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 13831TributylphosphineHCID 23610Benzene, 1-chloro-4-((chloromethyl)thio)-

Product 1

HCID 20386972Tributyl((4-chlorophenylthio)methyl)phosphonium chloride

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 8.45 g of tri(n-butyl)phosphine and 8.33 g of chloromethyl 4-chlorophenyl sulfide in 25 ml of p-dioxane was stirred and refluxed (101°-102° C.) for 20 hours. The mixture was cooled to room temperature and diluted with 100 ml of hexane. The white precipitate was filtered and dried to give 1, as a solid, mp 113°-114° C.

Workup

  1. temperaturerefluxed (101°-102° C.) for 20 hours
  2. filtrationThe white precipitate was filtered
  3. customdried
  4. customto give 1

Sources & evidence

ORD record
ord-c3b2990a92984880a10a534b9361c913
Source dataset
uspto-grants-1979_11
Patent number
US04173463

Reaction notes

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