Styrene → (1,1,3-Trichloro-3-phenylpropyl)phosphonic dichloride

HRID 1438899

Reaction equation

HRID 1438899 reaction equation
[Cl:1][C:2]([Cl:8])(Cl)[P:3]([Cl:6])([Cl:5])=[O:4].[CH2:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-:17].C([NH+](CC)CC)C>C(#N)C>[Cl:1][C:2]([Cl:8])([P:3]([Cl:6])([Cl:5])=[O:4])[CH2:9][CH:10]([Cl:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7501StyreneHCID 277422(Trichloromethyl)phosphonic dichlorideHCID 12698378Triethylazanium chloride

Product 1

HCID 21399673(1,1,3-Trichloro-3-phenylpropyl)phosphonic dichloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

11.8 g (0.05 mole) trichloromethane phosphonic dichloride, 7.8 g (0.075 mole) styrene, 134 mg (1 mmole) anhydrous cupric chloride and 206 mg triethylammonium chloride were brought into solution by 5 ml acetonitrile, and heated in the absence of air in a sealed ampoule at 110° during 3.5 hours. After cooling and opening of the ampoule, the reaction mixture was subjected to fractionation in vacuo, through a short Vigreux column. 9.1 g pure 1:1 adduct, 1,1,3-trichloro-3-phenyl-propane-1-phosphonic dichloride was obtained bp/0.05: 121°. Found: Cl: 50.8, Calc. for C9H8Cl5OP: 52.1%

Workup

  1. temperatureheated in the absence of air in a sealed ampoule at 110° during 3.5 hours
  2. temperatureAfter cooling

Sources & evidence

ORD record
ord-e8bc554633f140549bd5366045338224
Source dataset
uspto-grants-1977_11
Patent number
US04057578

Linked notes

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