Water → Benzyl 2-(2-fluoro-4-nitrobenzamido)acetate

Participants

Reaction Conditions

Reaction Steps

A mixture of spray-dried KF (200 mg, 3.48 mmol), intermediate 1 (250 mg, 0.696 mmol) and catalytic amount of 18-crown-6 in dry DMSO (5 mL) was stirred at 140-150° C. for 30 min. After completion (TLC), the reaction mixture was poured into ice cooled water (100 mL) and stirred for 5 min. The solution was extracted with EtOAc (3×50 mL). The combined solution was dried over anhyd Na2SO4. The solution was filtered and evaporated the solvents. The residue was chromatographed over silica gel column using hexane:acetone (80:20) as eluents to give the product as a pale yellow color solid (106 mg, 46%), mp 104-106° C. 1H NMR (400 MHz, CDCl3): δ 8.30 (1H, t, J=8.0 Hz), 8.13 (1H, dd, J=8.6, 1.4 Hz), 8.04 (1H, dd, J=11.0, 1.8 Hz), 7.38 (5H, s), 5.25 (2H, s), 4.33 (2H, d, J=4.8 Hz); LC-MS (negative ion mode): m/z 331 (M−H)−.

Provenance & Evidence