Nitrogen → HCID 88174277, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(4-fluorobenzyl)-1H-benzotriazole (91 mg) in THF (5 mL) at −78° C. was pumped under high vacuum for 5 min., then N2 was introduced in the reaction vessel. A solution of 0.98M n-BuLi in hexanes (0.41 mL) was then added, and the solution turned deep blue immediately. After stirring for 5 min at −78° C., a solution of (2-bromo-4-bromomethylphenyl)difluoromethylphosphonic acid di-tert-butyl ester (Example 1, Step 6)(157 mg) in THF (1.5 mL) was added. The deep blue color disappeared. The mixture was then stirred at −78° C. for 15 min then quenched with H2O and extracted with EtOAc. The EtOAc extract was washed with brine, dried (MgSO4) and concentrated. Chromatography over silica gel and elution with hexane:EtOAc (65:35, 0.2% Et3N), provided 85 mg of the intermediate.

Provenance & Evidence