Cyanomethylenetributylphosphorane → 1-Benzhydryl-3-[5-bromo-2-(3-chloro-benzyloxy)-phenoxy]-3-methyl-azetidine

Participants

Role	Name	HCID	Charge
Reactant	Cyanomethylenetributylphosphorane	HCID 4622928	—
Reactant	1-Benzhydryl-3-methylazetidin-3-ol	HCID 10243989	—
Reactant	HCID 67347295	HCID 67347295	—
Solvent	Toluene	HCID 1140	—
Product	1-Benzhydryl-3-[5-bromo-2-(3-chloro-benzyloxy)-phenoxy]-3-methyl-azetidine	HCID 67348353	43.7%

Reaction Conditions

Temperature	150 °C

Reaction Steps

The mixture of the title compound from Step A (0.5 mmol), 5-bromo-2-(3-chloro-benzyloxy)-phenol (0.5 mmol), and cyanomethylenetri-n-butylphosphorane (0.5 mmol) in toluene (3 mL) was heated at 150° C. in a microwave reactor for 1 h. The mixture was cooled to rt and purified via PTLC providing the title compound (120 mg). MS (ESI): mass calcd. for C30H27BrClNO2, 547.1; m/z found, 548.0 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08642583B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-2459de9a057140f6bdde4ce0d97113d0
Source note	uspto-grants-2014_02