Potassium Phosphate, Tribasic → HCID 58071477, compound

HRID 1256024Notes

Reaction equation

HRID 1256024 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[PH:13](=[O:20])([O:17]CC)[O:14][CH2:15][CH3:16].P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([P:13](=[O:17])([OH:20])[O:14][CH2:15][CH3:16])[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 811105-Chloro-2-nitroanisoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 178476833HCID 178476833, compound

Product 1

HCID 58071477HCID 58071477, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

4-Chloro-2-methoxy-1-nitrobenzene (4.84 g, 25.8 mmol) and diethyl phosphonate (3.92 g, 28.4 mmol) were added in a 250 mL round-bottomed flask. DMF (100 mL) was added to give a yellow solution. Potassium phosphate (6.02 g, 28.4 mmol) and palladium (II) acetate (0.290 g, 1.29 mmol) were added. Nitrogen was bubbled through the solution for 20 min before xantphos (1.045 g, 1.81 mmol) was added. The reaction was heated to 130° C. and stirred at that temperature for 4 h. After it was cooled to RT, the solution was concentrated in vacuo to remove the solvent, and to the residue was added water (60 mL) and DCM (40 mL). After partition, the aqueous layer was washed with DCM (2×20 mL). The aqueous layer was acidified using 12 N HCl (10 mL), and DCM was added (50 mL). After partition and extraction with DCM (2×30 mL), the DCM solution was combined and concentrated to give the product without further purification (2.4 g, 36% yield).

Workup

  1. customto give a yellow solution
  2. additionwas added
  3. temperatureAfter it was cooled to RT
  4. concentrationthe solution was concentrated in vacuo
  5. customto remove the solvent
  6. additionto the residue was added water (60 mL) and DCM (40 mL)
  7. customAfter partition
  8. washthe aqueous layer was washed with DCM (2×20 mL)
  9. additionwas added (50 mL)
  10. customAfter partition
  11. extractionextraction with DCM (2×30 mL)
  12. concentrationconcentrated
  13. customto give the product
  14. customwithout further purification (2.4 g, 36% yield)

Sources & evidence

ORD record
ord-48af340d649f423fb1fd1a0ebb0338a4
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

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