Triphenylphosphine → 3-Fluoro-2-nitro-N-(triphenylphosphoranylidene)benzenamine

HRID 1945605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1945605
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[N+:11]([O-:13])=[O:12])=[N+]=[N-].[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1.O>[F:10][C:6]1[C:5]([N+:11]([O-:13])=[O:12])=[C:4]([N:1]=[P:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:9]=[CH:8][CH:7]=1

Komponenten

5

Edukt 2

HCID 11776TriphenylphosphineHCID 220529091-Azido-3-fluoro-2-nitrobenzene

Produkt 1

HCID 596055033-Fluoro-2-nitro-N-(triphenylphosphoranylidene)benzenamineAusbeute 73,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-azido-3-fluoro-2-nitrobenzene (500 mg, 2.75 mmol) in THF (4 mL) and water (1 mL) was added triphenylphosphine (720 mg, 2.75 mmol). The reaction mixture was stirred at room temperature for 45 min then partitioned between water and EtOAc. The organic layer was separated and washed with brine, dried over Na2SO4, filtered and concentrated. The residue was subjected to flash chromatography (Si—PCC, Et2O) to give the desired product as a yellow solid (844 mg, 73%). LCMS (Method A): RT 4.36 min; [M+H]+ 417

Aufarbeitung

  1. customthen partitioned between water and EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bedd6c4143154ae2ac6029fdd19efc48
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394796B2

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