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

HRID 1472067Notes

Reaction equation

HRID 1472067 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-a44e7c7f412c4596ac2e1e3f3153791f
Source dataset
uspto-grants-2015_04
Patent number
US09012462B2

Reaction notes

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