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

HRID 1471981Notes

Reaction equation

HRID 1471981 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-e0c269cbc7ec44d0b0e00d598afc43f5
Source dataset
uspto-grants-2015_04
Patent number
US09012462B2

Reaction notes

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