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Potassium Phosphate, Tribasic → Dimethylphosphoryl-2-(trifluoromethoxy)aniline

HRID 1472123
Notes
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Reaction equation

HRID 1472123 reaction equation
I[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][C:10]([F:13])([F:12])[F:11])[CH:3]=1.[CH3:14][PH:15](=[O:17])[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>[CH3:14][P:15]([NH:6][C:5]1[CH:7]=[CH:8][CH:2]=[CH:3][C:4]=1[O:9][C:10]([F:13])([F:12])[F:11])([CH3:16])=[O:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27613984-Iodo-2-(trifluoromethoxy)anilineHCID 178503022methylphosphonoylmethane

Product 1

HCID 86668831Dimethylphosphoryl-2-(trifluoromethoxy)aniline

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalyst
HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-iodo-2-(trifluoromethoxy)aniline (0.606 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) and acidified with HCl in methanol to afford the desired product as its hydrochloride salt (0.573 g, 98% 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-f05870d239a443f79acd925a79224712
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09012462B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes