Potassium Phosphate, Tribasic → (3-Methoxy-4-nitrophenyl)(dimethyl)phosphane oxide

HRID 1472102Notes

Reaction equation

HRID 1472102 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([O:8][CH3:9])[CH:7]=1.[CH3:13][PH:14](=[O:16])[CH3:15].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.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:9][O:8][C:6]1[CH:7]=[C:2]([P:14](=[O:16])([CH3:15])[CH3:13])[CH:3]=[CH:4][C:5]=1[N+:10]([O-:12])=[O:11]

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 178503022methylphosphonoylmethane

Product 1

HCID 67052712(3-Methoxy-4-nitrophenyl)(dimethyl)phosphane oxideYield 30%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-Chloro-2-nitroanisole (0.5 g, 2.67 mmol) in 5 mL of DMF was added dimethylphosphine oxide (0.229 g, 2.93 mmol), palladium acetate (30 mg, 0.13 mmol), XANTPHOS (0.092 g, 0.16 mmol) and potassium phosphate (0.623 g, 2.93 mmol). The mixture was purged with argon, and heated at 120° C. for 1811. The reaction mixture was basified with saturated sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was concentrated and purified by prep-HPLC to give the final product (0.16 g, 30% yield). MS/ES+: m/z=229.

Workup

  1. customThe mixture was purged with argon
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-26b69f2b71da4e8c8c9f199bfd831790
Source dataset
uspto-grants-2015_04
Patent number
US09012462B2

Reaction notes

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