Trifluoroacetic acid → 3,3-Bis(3-bromophenyl)azetidine

HRID 1429274Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1429274
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Br:26])[CH:21]=3)[CH2:11][N:10](P(=O)(OCC)OCC)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Br:26])[CH:21]=3)[CH2:9][NH:10][CH2:11]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 58032038Diethyl 3,3-bis(3-bromophenyl)azetidin-1-ylphosphonate

Produkt 1

HCID 666303673,3-Bis(3-bromophenyl)azetidineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of diethyl 3,3-bis(3-bromophenyl)azetidin-1-ylphosphonate (960 mg, 1.9 mmol) in anhydrous dichloromethane (5 mL) under N2 was added TFA (5 mL). The mixture was stirred at 20° C. for 3 h, then concentrated by rotary evaporation. The residue was dissolved in dichloromethane (20 mL) and washed with aq. NaHCO3 (30 mL). The organic layer was dried and concentrated to afford 595 mg of the title compound (1.6 mmol, 85%) as a yellow oil which was used directly to next step without purification. LC/MS: [M+1]=368.

Aufarbeitung

  1. concentrationconcentrated by rotary evaporation
  2. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  3. washwashed with aq. NaHCO3 (30 mL)
  4. customThe organic layer was dried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-11d4c049b7ec4776905a10d64a87aac0
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937150B2

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