Iodine → HCID 11845284, compound

Participants

Reaction Steps

To a solution of 8-fluoro-2H-1-benzopyran-5-carboxamide (4.46 g, 23.1 mmol) in ethyl acetate (220 mL), ethylene glycol (4.0 mL) and a solution of sodium nitrite (6.52 g, 92.4 mmol) in H2O (11 mL) were added followed by iodine (9.0 g, 34.7 mmol). The reaction mixture was refluxed for 24 hours and during this time H2O (22 mL) and ethylene glycol (4.0 mL) were added portionwise. The reaction mixture was cooled, diluted with ethyl acetate, washed with a 5% solution of NaS2O3, treated with brine, dried with MgSO4, filtered, and the solvent was removed in vacuo to give a crude yellow solid. The solid was recrystallized from absolute ethanol to give 1.3 g (24% yield) of sparkly yellow crystals as the title compound (mp 227.8-228.2° C.). EIMS (70 eV) m/z (relative intensity) 238 (57, M+), 221 (100), 192 (71), 191 (46), 190 (10), 148 (14), 109 (16), 94 (12).

Provenance & Evidence