Triethyl phosphite → Diethyl 3,3-bis(3-bromophenyl)azetidin-1-ylphosphonate

Temperatur

150 °C

To a solution of 3-azido-2,2-bis(3-bromophenyl)propyl methanesulfonate (1.3 g, 2.66 mmol) in anhydrous toluene (10 mL) and anhydrous THF (5 mL) under N2 was added triethyl phosphite (0.49 mL, 2.79 mmol) at 25° C. The mixture was stirred for 18 h. The reaction was concentrated by rotary evaporation in a dried apparatus. The residue was dried in vacuo, and used in the next reaction without further purification. The crude triethyl phosphorimidate was dissolved in anhydrous m-xylene (5 mL) under N2 and heated in an oil bath at 150° C. for 12 h. After cooled to room temperature, the solvent was removed by rotary evaporation (vacuum pump assisted) to give a thick light orange oil which was purified by prep-TLC (eluent with EtOAc: dichloromethane=1:5) to afford 960 mg of diethyl 3,3-bis(3-bromophenyl)azetidin-1-ylphosphonate (1.9 mmol, 71% after two steps). LC/MS: [M+1]=504. 1HNMR (CDCl3), 400 MHz: δ 1.25-1.36 (m, 6H), 4.05-4.39 (m, 4H), 4.40 (d, 2H, J=5.2

1. concentrationThe reaction was concentrated by rotary evaporation in a dried apparatus
2. customThe residue was dried in vacuo
3. customused in the next reaction without further purification
4. temperatureAfter cooled to room temperature
5. customthe solvent was removed by rotary evaporation (vacuum pump assisted)
6. customto give a thick light orange oil which
7. customwas purified by prep-TLC (eluent with EtOAc: dichloromethane=1:5)

ORD-Eintrag

ord-2aaff5b6d3144870b914c438c391d18e

Quelldatensatz

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08937150B2