Chlorosuccinimide → HCID 86707795, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-[4-(hydroxyimino-methyl)-phenyl]-azetidine-3-carboxylic acid methyl ester (Preparation 10, 2.36 g, 10.08 mmol) in DMF (25 mL) was added N-chloro succinimide (1.48 g, 11.09 mmol) at 0° C. Resulting reaction mixture was stirred at 0° C. for 1 hour and then at 10° C. for 1 hour. After complete consumption of starting material to chloro intermediate (red colored reaction mixture) potassium hydrogen carbonate (1.51 g, 15.12 mmol, 1.5 eq.) was added followed by of 1,2,3-trichloro-5-(1-trifluoromethyl-vinyl)benzene (1.21 g, 12.10 mmol) at room temperature. Resulting reaction mixture was stirred at room temperature for 4 hours under nitrogen atmosphere. After consumption of chloro intermediate, reaction mixture was quenched with water (200 mL) and extracted with EtOAc (2×200 mL). Combined organic layer was washed with water (2×400 mL), brine (2×200 mL), dried over anhydrous sodium sulphate and concentrated in vacuo to afford brown colored semi solid (2.5 g, crude). Crude compound was purified by column chromatography (silica gel, 100-200 mesh). Compound was eluted using 25% ethyl acetate in hexane to afford off white solid (1.91 g, 33%). 1H NMR (400 MHz, CDCl3): 3.58-3.63 (m, 2H), 3.75 (s, 3H), 4.03 (d, 1H, J=17.04 Hz), 4.07-4.15 (m, 4H), 6.39-6.42 (m, 2H), 7.46-7.49 (m, 2H), 7.63 (s, 2H); LC-MS (M+H): =506.90.

Provenance & Evidence