Thionyl Chloride → Diethyl [chloro(4-chlorophenyl)methyl]phosphonate

HRID 1460993Notes

Reaction equation

HRID 1460993 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])O)=[CH:4][CH:3]=1.S(Cl)([Cl:20])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[Cl:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 89363Diethyl P-((4-chlorophenyl)hydroxymethyl)phosphonate

Product 1

HCID 12881548Diethyl [chloro(4-chlorophenyl)methyl]phosphonateYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 38.0 grams (0.136 mole) of diethyl (4-chlorophenyl)hydroxymethylphosphonate in 250 ml of methylene chloride was cooled to 0° C., and a solution of 18.8 grams (0.158 mole) of thionyl chloride in 12 ml of methylene chloride was added via syringe. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature where it was stirred for 60 hours. After this time the reaction mixture was washed with two portions of aqueous 1N hydrochloric acid. The organic layer was filtered through silica gel. The silica gel was eluted with 1:1-hexane/ethyl acetate. The combined filtrates were concentrated under reduced pressure, yielding 40.5 grams of diethyl (4-chlorophenyl)chloromethylphosphonate. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. washAfter this time the reaction mixture was washed with two portions of aqueous 1N hydrochloric acid
  3. filtrationThe organic layer was filtered through silica gel
  4. washThe silica gel was eluted with 1
  5. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-0b8669e79bc047479ff789bf03d8dfb7
Source dataset
uspto-grants-1991_12
Patent number
US05073564

Reaction notes

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