Hydrochloric Acid → 1-(3-tert-Butyl-4-hydroxy-5-iodophenyl)ethanone

Participants

Reaction Steps

1-(3-tert-Butyl-4-hydroxyphenyl)ethanone (384 mg, 2 mmol) and sodium iodide (360 mg, 2.4 mmol) were dissolved in a mixed solution of N,N-dimethylformamide (3 mL) and water (1 mL), and this was cooled in an ice bath. While stirring, N-chlorosuccinimide (NCS) (320 mg, 2.4 mmol) was added portionwise over 10 minutes. After stirring for 50 minutes, 2% aqueous sodium thiosulfate (4 mL), 2 N hydrochloric acid (1 mL), and ethyl acetate (10 mL) were added, and the solution was separated. The organic layer was washed with a mixed solution of 2% aqueous sodium thiosulfate (5 mL) and saturated brine (1 mL), and then with saturated brine (5 mL). The organic layer was dried, and concentrated under reduced pressure (50° C.) to obtain 616 mg of the subject compound as a yellowish oily substance (yield: 96.8%, HPLC purity: 93.2%).

Provenance & Evidence