Chloroform → HCID 10870025, compound

HRID 350721Notes

Reaction equation

HRID 350721 reaction equation
O[CH:2]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.C(Cl)(Cl)Cl.C(N(S(F)(F)[F:30])CC)C>[Cl-].[Na+].O>[CH2:14]([O:13][P:12]([CH:2]([F:30])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1)([O:16][CH2:17][CH3:18])=[O:19])[CH3:15]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 123472(Diethylamino)sulfur trifluorideHCID 10661075HCID 10661075, compound

Product 1

HCID 10870025HCID 10870025, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of diethyl α-hydroxy-4-nitrobenzylphosphonate (1.0 g) and chloroform (10 mL) was added diethylaminosulfur trifluoride (1.4 mL) at −78° C. and the reaction mixture was warmed to room temperature. Saturated brine was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was concentrated and the residue was purified by preparative HPLC to give 4-[(diethylphosphono)(fluoro)methyl]nitrobenzene (0.1 g, yield 10%) as yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe extract was concentrated
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-cfc786b60e9b4791a28fc8362ed97531
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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