Oxidation and Bromodehydroxymethylation of Benzylic Alcohols using NaBrO3/NaHSO3 Reagent (Bull. Korean. Chem. Soc. 2002, Vol. 23, pp 1667)General procedureTo a stirred solution of alcohol (5 mmol) in aqueous acetonitrile (30mL, 1:1 by volume) was added NaBrO
3 (1.51g, 10 mmol) and NaHSO
3 (1.04g, 10 mmol). Reactions were continuously monitired by TLC and stirred at room temperature for the time indicated in Table 1. The reaction mixture was quenched with aqueous sodium thiosulfate and extracted with ether (3 × 30mL). The combined organic layers were washed with aqueous Na
2CO
3, water, dried over MgSO
4, filtered and concetrated in vacuo. The residue was chromatographed on a silica gel column and eluted with hexane-EtOAc (10:1) to give aldehyde or aryl bromide (Table 1). The combined aqueous layer was acidified with 10% HCl to pH 2 and extracted with EtOAc (2 × 50mL). The organic layers were washed with water, dried and evaporated to afford the products.