Methyl bromoacetate → HCID 57894613, compound

Participants

Reaction Conditions

Reaction Steps

N,N-Diisopropylethylamine (1.47 mL, 8.45 mmol) and then methyl bromoacetate (1.29 g, 8.45 mmol) were added to a solution of N-benzyl-3-chloro-4-fluoroaniline (7-1, 1.00 g, 4.23 mmol) in DMF (7 mL), and the resulting mixture was stirred at 50° C. for 2 h, 60° C. for 3 h, and then 50° C. for 18 h. Methyl bromoacetate (0.4 mL, 4 mmol) was added and mixture was heated to 60° C. for 7 h and then 50° C. for 18 h. The reaction was diluted with EtOAc (100 mL) and washed with saturated aqueous ammonium chloride (3×100 mL), H2O (100 mL), and brine (50 mL). The reaction was concentrated and purified residue by flash column chromatography (SiO2, 0-20% EtOAc/hexanes gradient) to provide methyl N-benzyl-N-(3-chloro-4-fluorophenyl)glycinate (7-2). 1H NMR (300 MHz, CDCl3) δ 7.38-7.25 (m, 5H), 6.97 (dd, J=8.9, 8.9 Hz, 1H), 6.69 (dd, J=6.1, 3.1 Hz, 1H), 6.50 (ddd, J=8.9, 3.4, 3.4 Hz, 1H), 4.59 (s, 2H), 4.05 (s, 2H), 3.76 (s, 3H).

Provenance & Evidence