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

HRID 921316Notes

Reaction equation

HRID 921316 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.P([O-])(OCC)[O:14]CC.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2[C:25]([P:29]([C:36]3C=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:29](=[O:14])([CH3:36])[CH3:25])[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 3780918Diethylphosphite

Product 1

HCID 67052712(3-Methoxy-4-nitrophenyl)(dimethyl)phosphane oxideYield 687.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-2-nitroanisole (1.00 g, 5.33 mmol) in 20 mL DMF was added diethyl phosphite (0.809 g, 5.86 mmol), palladium acetate (0.060 g, 0.27 mmol), XantPHOS (0.185 g, 0.320 mmol), and potassium phosphate (1.24 g, 5.86 mmol). The mixture was purged with nitrogen, and subjected to microwaves at 150° C. for 20 minutes. The reaction mixture was concentrated and purified by silica gel chromatography (0-45% ethyl acetate:heptane) to afford the desired product (0.504 g, 33% yield).

Workup

  1. customThe mixture was purged with nitrogen
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by silica gel chromatography (0-45% ethyl acetate:heptane)

Sources & evidence

ORD record
ord-58ffbd157f2e40ba81f48de628598acb
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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