Potassium Phosphate, Tribasic → (4-Amino-3-chlorophenyl)dimethylphosphine oxide

HRID 921459Notes

Reaction equation

HRID 921459 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7](I)[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:10][PH:11](=[O:13])[CH3:12].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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>[Cl:1][C:2]1[CH:8]=[C:7]([P:11]([CH3:12])([CH3:10])=[O:13])[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2829302-Chloro-4-iodoanilineHCID 178503022methylphosphonoylmethane

Product 1

HCID 67052677(4-Amino-3-chlorophenyl)dimethylphosphine oxideYield 83.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-4-iodoaniline (0.507 g, 2.00 mmol) in 8 mL DMF was added dimethylphosphine oxide (0.171 g, 2.20 mmol), palladium acetate (22.4 mg, 0.0100 mmol), XANTPHOS (69.4 mg, 0.120 mmol), and potassium phosphate (0.467 g, 2.20 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 (0-20% 7N ammonia in methanol:dichloromethane) to afford the desired product (0.340 g, 83% yield).

Workup

  1. customThe mixture was purged with nitrogen
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by silica gel chromatography (0-20% 7N ammonia in methanol:dichloromethane)

Sources & evidence

ORD record
ord-17f9707515b44d76ba181968fdbc5324
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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