Synthesis of (Diacetoxyiodo)benzene

(Diacetoxyiodo)benzene; Large-Scale Synthesis:

K2S2O8 (100 mmol) was slowly added portion-wise over 20 min to a stirred solution of an iodobenzene (5.10 g, 25 mmol) in AcOH (125 mL) with concd H2SO4 (100 mmol) at r.t. (25 °C), and the mixture was stirred at r.t. for 4 h. The solution was then concentrated to half its volume by evaporation of AcOH under reduced pressure, and H2O (100 mL) was added. The precipitate formed was collected by filtration, washed with H2O (200 mL), and dried in air. A second crop of product was obtained by extraction of the filtrate with CH2Cl2 (3 × 25 mL); the combined extracts were dried over anhyd Na2SO4, filtered, and concentrated under reduced pressure. The combined crude products were purified by recrystallization from AcOH–hexane; yield: 7.15 g (88.7%).

Reference:

Synthesis 2005, No. 12, 1932–1934