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ABBX, A Highly Active Trivalent Iodine Compound for Oxidation Reactions
No.162(July 2014)
1-Acetoxy-5-bromo-1,2-benziodoxol-3(1H)-one (1, ABBX) is a highly active trivalent iodine compound developed by Togo et al.1) 1 oxidizes aliphatic primary and secondary alcohols to the corresponding aldehydes and ketones in good yields. 5-Bromo-2-iodobenzoic acid, formed as a co-product of this reaction, can be recovered by acidification of the aqueous layer. 1 has chemically similar activity to “Super DIB” (ANBX) which was introduced in TCIMAIL number157 p.8, and has more solubility in organic solvents than Super DIB.1,2)
Typical Procedure (oxidation of 4-methylbenzyl alcohol to 4-methylbenzaldehyde): To a solution of 4-methylbenzyl alcohol (1.0 mmol, 122.1 mg) in CHCl3 (4 mL) is added ABBX (2.0 mmol, 767.7 mg). The mixture is stirred at 60 °C for 24 h. After the reaction is completed, the reaction mixture is added to aq. NaHCO3 (10 mL). The aqueous layer is extracted with CHCl3 (3 × 10 mL), and the organic layer is dried over Na2SO4. The filtrate is concentrated under reduced pressure to give 4-methylbenzaldehyde (108.0 mg, 90% yield) with 90% purity. The aqueous layer is acidified (pH ca. 2) with 1 M aq. HCl (15 mL) and the obtained mixture is filtered to afford 2-iodo-5-bromobenzoic acid (593 mg, 91%).
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