1,3-Butadiene → 1,1,5-Trichloro-pent-3-ene-1-phosphonic dichloride

HRID 1438906Notes

Reaction equation

HRID 1438906 reaction equation
[Cl:1][C:2]([Cl:8])(Cl)[P:3]([Cl:6])([Cl:5])=[O:4].[CH2:9]=[CH:10][CH:11]=[CH2:12].[Cl-:13].C([NH+](CC)CC)C>C(Cl)Cl>[Cl:1][C:2]([Cl:8])([P:3]([Cl:6])([Cl:5])=[O:4])[CH2:9][CH:10]=[CH:11][CH2:12][Cl:13]

Participants

5

Reactant 3

HCID 78451,3-ButadieneHCID 277422(Trichloromethyl)phosphonic dichlorideHCID 12698378Triethylazanium chloride

Product 1

HCID 541714891,1,5-Trichloro-pent-3-ene-1-phosphonic dichloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

11.8 g (0.05 mole) trichloromethane phosphonic dichloride was dissolved in 10 ml dry methylene chloride, cooled, and a cold solution of 4 g butadiene in 10 ml methylene chloride, which also contained 134 mg (1 mmole) anhydrous cupric chloride and 206 mg (1.5 mmole) triethylammonium chloride, was added. The resulting homogeneous solution was heated in the absence of air, in a sealed ampoule, at 100° for 8 hours. After cooling, the reaction product was freed from solvent, and fractionated through a short Vigreux column. 9.6 g pure 1:1 adduct, 1,1,5-trichloro-pent-3-ene-1-phosphonic dichloride was obtained, bp/0.05: 92°-93°. Found: Cl: 61.3%, Calc. for C5H6Cl5OP: 61.0%.

Workup

  1. temperaturecooled
  2. temperatureThe resulting homogeneous solution was heated in the absence of air
  3. temperatureAfter cooling

Sources & evidence

ORD record
ord-c3a372ae296944d0bd393fb4b8296377
Source dataset
uspto-grants-1977_11
Patent number
US04057579

Reaction notes

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