Acetic Acid → HCID 86626432, compound

Participants

Reaction Steps

To a solution of 4-bromobenzaldehyde (3.70 g, 20 mmol) in ethanol (30 mL) was added 50% aqueous hydroxylamine (1.25 mL, 21 mmol) and glacial acetic acid (1.25 mL, 21 mmol). After 30 minutes, the reaction mixture was diluted with ethyl acetate and washed with water and with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated to leave a white solid. To a solution of this solid in tetrahydrofuran (80 mL) and 1,3-dichloro-5-[1-(trifluoromethyl)ethenyl]benzene (i.e. the product from Example 1, Step A) (4.82 g, 20 mmol) was added an aqueous solution of sodium hypochlorite (6.15%—Clorox® brand) (80 mL) dropwise over 1 h. The reaction mixture was stirred at ambient temperature for 16 h. The phases were separated, and the aqueous phase was extracted once with diethyl ether. The combined organic phases were washed with saturated aqueous sodium bisulfite solution and saturated aqueous sodium chloride solution, and dried over magnesium sulfate, and concentrated to leave a white solid. This solid was triturated with warm (40° C.) hexanes, allowed to cool, and solids were collected on a glass frit and dried to obtain the title product as a white solid (5.25 g).

Provenance & Evidence