Acetic Acid → HCID 178501035, compound

Participants

Reaction Steps

Sulfuric acid (0.708 mL, 13.29 mmol) was added into a cold (ice bath) mixture of methyl trans-4-(4-chlorophenyl)cyclohexanecarboxylate (3.3588 g, 13.29 mmol) and n-iodosuccinimide (2.99 g, 13.29 mmol) in acetic acid (0.798 g, 13.29 mmol). The reaction mixture was stirred in an ice bath and was allowed to warm to ambient temperature overnight. The reaction crude was poured into an ice water and extracted with EtOAc. The separated organic phase was dried over Na2SO4, filtered and evaporated to afford a dark mixture. The resulting crude mixture was purified by flash chromatography (SiO2, Biotage 65i cartridge). The column was eluted by a EtOAc/hexanes mixture (0% to 10%). Related fractions were pooled and evaporated to afford a crystalline solid as the titled compound. LCMS calc.=377.99. found=379.00 (M+H)+.

Provenance & Evidence