Tetrabutylammonium Fluoride → 5-Ethynyl-2-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methyl-5-((trimethylsilyl)ethynyl)benzamide (170) (0.190 g, 0.819 mmol) in THF (4 mL) at 0° C. was added 1.0 M solution TBAF in THF (0.5 mL). The mixture was then stirred under N2 at 0° C. for 10 minutes and then at room temperature for 3 hours. The resulting mixture was concentrated under reduced pressure then diluted with water. The resulting precipitate was collected by vacuum filtration to give the title compound (I71) (0.087 g, 67%); 1H NMR (400 MHz, d6-DMSO) δ 7.80 (s, 1H), 7.41 (m, 3H), 7.25 (d, J=7.7 Hz, 1H), 4.17 (s, 1H), 2.36 (s, 3H).

Provenance & Evidence