Water → di-O-isopropyl P-[[(2-trifluoromethyl-6-methylphenyl)sulfonyloxy]methyl]phosphonate

HRID 1379300Notes

Reaction equation

HRID 1379300 reaction equation
[OH-].[Na+].O.[OH:4][CH2:5][P:6](=[O:15])([O:11][CH:12]([CH3:14])[CH3:13])[O:7][CH:8]([CH3:10])[CH3:9].[F:16][C:17]([F:30])([F:29])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1[S:25](Cl)(=[O:27])=[O:26]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[F:30][C:17]([F:16])([F:29])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1[S:25]([O:4][CH2:5][P:6](=[O:15])([O:7][CH:8]([CH3:10])[CH3:9])[O:11][CH:12]([CH3:14])[CH3:13])(=[O:27])=[O:26]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 10867235Diisopropyl hydroxymethylphosphonateHCID 11032589145980-57-0

Product 1

HCID 18981706di-O-isopropyl P-[[(2-trifluoromethyl-6-methylphenyl)sulfonyloxy]methyl]phosphonateYield 94.8%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent2×

Procedure

A mixture of 100 mL of toluene, 11.6 g of 50% aqueous sodium hydroxide solution, and 10 mL of water was cooled in an ice bath and treated with 1.3 g of benzyltriethylammonium chloride and 12.0 g of diisopropyl P-(hydroxymethyl)phosphonate (prepared as in U.S. Pat. No. 5,272,128) and stirred vigorously. To this was added a solution of 15 g of the compound of Example 16 (2-trifluoromethyl-6-methylbenzenesulfonyl chloride) in 10 mL of toluene. The cooling bath was removed and the mixture stirred for one hour, then the layers were separated. The organic phase was washed with water (2×100 mL) and brine, then dried through calcium sulfate to yield 23 g of di-O-isopropyl P-[[(2-trifluoromethyl-6-methylphenyl)sulfonyloxy]methyl]phosphonate as a brown oil.

Workup

  1. temperaturewas cooled in an ice bath
  2. customprepared as in U.S
  3. customThe cooling bath was removed
  4. stirringthe mixture stirred for one hour
  5. customthe layers were separated
  6. washThe organic phase was washed with water (2×100 mL) and brine
  7. dry with materialdried through calcium sulfate

Sources & evidence

ORD record
ord-140f843c4fa241a59177c71f7bba39ac
Source dataset
uspto-grants-1997_09
Patent number
US05670691

Reaction notes

Loading…