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

HRID 1438900Notes

Reaction equation

HRID 1438900 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-e853973cd3c74b0e94fcf182e4c51b54
Source dataset
uspto-grants-1977_11
Patent number
US04057578

Reaction notes

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