18-Crown-6 → HCID 59864777, compound

Participants

Reaction Conditions

Reaction Steps

Under an N2 atmosphere, 5-fluoro-2-methyl-4-nitro-1H-benzo[d]imidazole (0.233 g, 1.19 mmol) was treated with Al2O3 supported potassium fluoride (0.583 g, 40 wt. %), 3-chloro-4-hydroxyphenylacetic acid (0.223 g, 1.19 mmol) and 18-crown-6 (0.031 g, 0.119 mmol) in DMSO (1 mL). The reaction was heated 80° C. for 20 h. Upon cooling to room temperature, the reaction was diluted with water and 1N HCl was added to pH 5. The reaction was extracted with ethyl acetate (3×). The organics were combined, dried (Na2SO4), filtered and concentrated in vacuo. Flash column chromatography of the residue, eluting with 0% to 10% methanol in dichloromethane, afforded the title compound. LC-MS ESI (pos.) m/z: 362.0 (M+H).

Provenance & Evidence