Tetrabutylammonium Fluoride → N-(5-Ethynyl-2-methylphenyl)-2,2,2-trifluoroacetamide

Participants

Reaction Steps

To a solution of 2,2,2-trifluoro-N-{2-methyl-5-[(trimethylsilyl)ethynyl]phenyl}-acetamide (10.9 g, 36 mmol) in THF (350 mL) cooled to 0° C. was added a 1M solution of tetrabutylammonium fluoride in THF (40 mmol, 40 mL). The reaction was diluted with water and extracted two times with EtOAc. The combined organic extractions were washed with water, dried over MgSO4 and concentrated onto silica gel. The crude material was purified by column chromatography to give the desired product (6.4 g, 78%). 1H NMR (400 MHz, d6-DMSO) δ 11.00 (s, 1H), 7.36-7.30 (m, 3H), 4.19 (s, 1H), 2.17 (s, 3H) ppm.

Provenance & Evidence