Triethylamine → HCID 58696172, compound

Participants

Reaction Steps

8.55 g (48 mmol) of 2-fluoro-5-trifluoromethylaniline and 4.8 g (48 mmol) of triethylamine were dissolved in 30 mL of dry DCM and added dropwise to a solution of 4.7 g (16 mmol) of triphosgene in 30 mL of DCM at 5-10° C. Within 20 min TLC indicated full consumption of the starting amine. This mixture was treated dropwise with a solution of 11.3 g (48 mmol) of 2-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine and 4.8 g of triethylamine in 35 mL of DCM at room temperature. Then the reaction mixture was stirred for 2 h, poured into water, the organic layer was separated and evaporated. The residue was crystallized from 90% EtOH yielding 4.5 g of the target product. Flash column chromatography of the residue obtained from evaporation of the mother liquid yielded 2.7 g of the target material (combined yield 7.2 g; 34%).

Provenance & Evidence