Potassium Phosphate, Tribasic → HCID 86668805, compound

HRID 1472074Notes

Reaction equation

HRID 1472074 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:13]([O-:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16].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:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])[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 86668805HCID 86668805, compoundYield 33%

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-73fe3990c18946fd9389128bea74e4c7
Source dataset
uspto-grants-2015_04
Patent number
US09012462B2

Reaction notes

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