Trifluoroacetic acid → 1-(1-Azido-1-methylethyl)-3,5-difluorobenzene

HRID 1808209

Reaktionsgleichung

[NH:1]=[N+:2]=[N-:3].[F:4][C:5]1[CH:6]=[C:7]([C:12](O)([CH3:14])[CH3:13])[CH:8]=[C:9]([F:11])[CH:10]=1.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[N:1]([C:12]([C:7]1[CH:8]=[C:9]([F:11])[CH:10]=[C:5]([F:4])[CH:6]=1)([CH3:14])[CH3:13])=[N+:2]=[N-:3]

Komponenten

Reaktionsbedingungen

Temperatur: -5 °C

Versuchsvorschrift

Hydrogen azide (2M in toluene, 1.5 mol) was added to the solution of 2-(3,5-difluoro-phenyl)-propan-2-ol (Preparation 50, 145 g, 0.84 mol, 1 eq) in chloroform (1 L) and the content of the flask was cooled to −5° C. The mixture of TFA (2.5 mol, 2.98 eq) with chloroform (1:1) was added dropwise at such a rate to keep the internal temperature below −5° C. After the addition was complete, the reaction mixture was allowed to warm to room temperature and stirring was continued for 20 h. The reaction was poured into 2M sodium hydroxide and layers were separated. The aqueous phase was extracted two times with chloroform and combined organic extracts were washed with brine and dried over anhydrous magnesium sulfate. After removal of the solvent, the title compound was used in the next step without further purification (171 g, 0.87 mol, 100%).

Aufarbeitung

additionwas added dropwise at such a rate
customthe internal temperature below −5° C
additionAfter the addition
temperatureto warm to room temperature
customwere separated
extractionThe aqueous phase was extracted two times with chloroform
washwere washed with brine
dry with materialdried over anhydrous magnesium sulfate
customAfter removal of the solvent
customthe title compound was used in the next step without further purification (171 g, 0.87 mol, 100%)

Quellen und Nachweise

ORD-Eintrag: ord-c707ead22b7345c08a5019d8b7e68bc3
Quelldatensatz: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08357711B2

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