Dimethylformamide → HCID 86712672, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of methyl 2-(2-bromo-4-(trifluoromethyl)phenyl)acetate (A57) (1.60 g, 5.38 mmol), PdCl2(PPh3)2 (189 mg, 269 μmmol), t-Bu3PH.BF4 (78.1 mg, 269 μmmol), CuI (51.3 mg, 269 μmol) and TMS-acetylene (1.52 mL, 10.8 mmol) in Et3N (10 mL) and anhydrous, degassed DMF (10 mL) was stirred at 80° C. for 16 hours. The resulting mixture was adsorbed onto silica gel and purified using column chromatography (Biotage Isolera, SiO2 cartridge, 0-10% EtOAc in petroleum benzine 40-60° C.) to give the title compound A58 as an orange liquid (1.56 g, 92%); 1H NMR (400 MHz, CDCl3) δ 7.73 (d, J=1.1 Hz, 1H), 7.53 (dd, J=8.1, 1.3 Hz, 1H), 7.39 (d, J=8.1 Hz, 1H), 3.87 (s, 2H), 3.71 (s, 3H), 0.26 (s, 9H). LCMS-A: rt 6.979 min; m/z 315 [M+H]+.

Provenance & Evidence