Pyridine → HCID 12874240, compound

HRID 1447438Notes

Reaction equation

HRID 1447438 reaction equation
S(Cl)(Cl)=O.[CH2:5]([O:7][P:8]([CH:13](O)[C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=1)(=[O:12])[O:9][CH2:10][CH3:11])[CH3:6].C(Cl)[Cl:27].N1C=CC=CC=1>O>[CH2:5]([O:7][P:8]([CH:13]([Cl:27])[C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=1)(=[O:12])[O:9][CH2:10][CH3:11])[CH3:6]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 12874245HCID 12874245, compound

Product 1

HCID 12874240HCID 12874240, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

8.7 g (0.073 mol) of thionyl chloride were added to a mixture of 22.96 g (0.07 mol) of 4-trifluoromethoxy-α-hydroxy-benzylphosphonic acid diethyl ester, 70 ml of methylene chloride and 5.6 g (0.07 mol) of pyridine at 20°-40° C. in the course of about 1 hour, while cooling slightly with water. The reaction mixture was then heated to 50° C. for 3 hours and was subsequently stirred for 12 hours without further action of heat. The mixture was poured onto about 100 g of ice-water and the organic phase was separated off and dried. After distilling off the solvent, the residue was concentrated under 2 mm Hg and at 45° C. 18.7 g (77.1% of theory) of 4-trifluoromethoxy-α-chloro-benzyl-phosphonic acid diethyl ester were obtained as a yellow viscous oil with a refractive index of nD22 : 1.4968.

Workup

  1. temperatureof heat
  2. customthe organic phase was separated off
  3. customdried
  4. distillationAfter distilling off the solvent
  5. concentrationthe residue was concentrated under 2 mm Hg and at 45° C

Sources & evidence

ORD record
ord-e266e36ccc1846cfa7fd83885533c6cf
Source dataset
uspto-grants-1982_02
Patent number
US04316913

Reaction notes

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