Water → HCID 76688559, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-fluoro-3-iodo4-methylbenzaldehyde oxime (0.48 g, 1.7 mmol) in DMF (0.5 mL) was added N-chlorosuccinimide (83 mg, 0.62 mmol) and the mixture was heated at 55° C. for 5 min. The mixture was allowed to cool to <50° C., an additional N-chlorosuccinimide (166 mg, 1.24 mmol) was added, then it was heated at 55° C. for 10 min. The reaction mixture was allowed to cool to RT, treated with water (5 mL), and extracted with ethyl acetate (3×20 mL). The combined ethyl acetate layers were washed with brine, dried and concentrated to afford the intermediate, 2-fluoro-3-iodo-4-methylbenzoyl chloride oxime as a light yellow amorphous solid, which was used without further purification. MS (ESI, pos. ion) m/z: 314.3 (M+1). Cyclopropylamine (0.60 mL, 8.6 mmol) was added dropwise to an ice-cold solution of the above obtained 2-fluoro-3-iodo-4-methylbenzoyl chloride oxime in anhydrous THF (2 mL). The reaction mixture was stirred at ambient for 3 h. The volatiles were removed under reduced pressure and the residue purified on a 40 g ISCO column (eluted with 25-60% ethyl acetate in Hexanes) to provide the title compound as an amorphous off-white solid. MS (ESI, pos. ion) m/z: 335.0 (M+1).

Provenance & Evidence