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Potassium Phosphate, Tribasic → 4-(Dimethylphosphoryl)-2-fluoroaniline

HRID 921461
Notes
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Reaction equation

HRID 921461 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[CH3:10][PH:11](=[O:13])[CH3:12].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>[CH3:10][P:11]([C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1)([CH3:12])=[O:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 1230504-Bromo-2-fluoroanilineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 178503022methylphosphonoylmethane

Product 1

HCID 670526804-(Dimethylphosphoryl)-2-fluoroanilineYield 20%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-2-fluoroaniline (0.380 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 (73.5 mg, 20% 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-3c274edf305248fa9d32f90fd74287d6
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09273077B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes