120363-13-5

619-58-9

865-47-4

120363-13-5

The general procedure for the synthesis of tert-butyl p-iodobenzoate from 4-iodobenzoic acid and potassium tert-butoxide was as follows: first, thionyl chloride (2.30 mL, 32.30 mmol) and N,N-dimethylformamide (DMF) (0.02 mL, 0.20 mmol) were added to 4-iodobenzoic acid (1.00 g, 4.00 mmol). Subsequently, the air in the reaction system was displaced with nitrogen and the mixture was heated to 75 °C and kept at reflux while stirring for 1 hour. After completion of the reaction, the reaction solution was concentrated under reduced pressure. The obtained residue was dissolved in tetrahydrofuran (THF) (5 mL), and then a 1 M THF solution of potassium tert-butanolate (4.5 mL) was slowly added at low temperature and stirring was continued for 30 min. After that, the reaction solution was again concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate and washed sequentially with water and brine. The organic layer was collected, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure. Finally, the concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate = 9:1) to afford the target product tert-butyl p-iodobenzoate (14.00 g, 99.9% yield). The product was confirmed by 1H NMR (CDCl3, 400 MHz): δ 7.77 (2H, d, J = 7.5 Hz, aromatic), 7.69 (2H, d, J = 8.0 Hz, aromatic), 1.59 (9H, s, (CH3)3).