Diisopropyl bromomethylphosphonate → HCID 11322769, compound

HRID 1048467Notes

Reaction equation

HRID 1048467 reaction equation
Br[CH2:2][P:3](=[O:12])([O:8][CH:9]([CH3:11])[CH3:10])[O:4][CH:5]([CH3:7])[CH3:6].[C:13]([O-:16])(=[S:15])[CH3:14].[K+]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:13](=[O:16])([S:15][CH2:2][P:3]([O:8][CH:9]([CH3:11])[CH3:10])([O:4][CH:5]([CH3:7])[CH3:6])=[O:12])[CH3:14]

Participants

5

Reactant 2

HCID 4366885Diisopropyl bromomethylphosphonateHCID 23670855Potassium ethanethioate

Product 1

HCID 11322769HCID 11322769, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of diisopropyl bromomethylphosphonate (5.00 g, 19.3 mmol) in N,N-dimethylformamide (15.4 mL) was added potassium thioacetate (3.75 g, 32.8 mmol) followed by tetrabutylammonium iodide (0.36 g, 0.97 mmol). The reaction mixture was stirred at 85° C. for 2.5 hours. The reaction mixture was cooled and partitioned between water and EtOAc (3×) and the layers were separated. The combined organic layers were dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. Purification of the residue by flash chromatography on silica gel (24 g column, eluent: 0 to 90% EtOAc/hexanes) provided the title compound as an off-white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between water and EtOAc (3×)
  3. customthe layers were separated
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customPurification of the residue by flash chromatography on silica gel (24 g column, eluent: 0 to 90% EtOAc/hexanes)

Sources & evidence

ORD record
ord-170bacf4527e4044900ac29f45c8f8d0
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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