Trifluoroacetic acid → HCID 59557146, compound

Participants

Reaction Steps

To a slurry of hexanes-washed NaH (0.492 g of a 60% w/w suspension in mineral oil, 12.3 mmol) in dry DMF (10 mL) at 0° C. was added a solution of 4-bromo-N-(2,2,2-trifluoroethyl)-2-(trifluoromethyl)aniline (1.96 g, 6.13 mmol) in DMF (2 mL), dropwise over 5 min. The mixture was stirred 15 min and tert-butyl bromoacetate (1.82 mL, 12.3 mmol) was added dropwise over 1 min. The mixture was stirred overnight, slowly warming to rt. The mixture was poured into water and the whole was extracted with Et2O (×3). Combined organic portions were washed (water, brine), dried over Na2SO4, filtered and concentrated. The residue was dissolved in CH2Cl2 (20 mL) and to this solution was added Et3SiH (4.9 mL, 31 mmol) and TFA (20 mL). The mixture was stirred 1.5 h at rt and concentrated in vacuo. The residue was partitioned between water/Et2O and the layers were separated. The organic layer was concentrated in vacuo. The residue was purified by filtration through a pad of silica gel (10% EtOAc/hexanes, then EtOAc to elute carboxylic acid) affording 1.50 g of the title compound as a pale yellow solid: MS (APCI) m/z 380 ([M−H]−, 81Br), 378 ([M−H]−, 79Br).

Provenance & Evidence