Iodine → 1-Bromo-3-Iodo-2-hydroxymethyl naphthalene

Participants

Reaction Steps

A suspension of thalium trifluoro acetate (1.37 g, 2.53 mmole) in anhydrous CCl4 containing 24 (0.5 g, 2.1095 mmole) was refluxed under argon. Iodine (0.535 g, 2.1095 mmole) was added dropwise in a solution of CCl4 (10 ml). The mixture was refluxed for another 60 min. The reaction was cooled and quenched with 10% solution of sodium thiosulfate and then extracted with 3×50 ml of methylene chloride. The combined methylene chloride fractions were thoroughly washed several times with H2O, brine, dried with anhydrous magnesium sulfate, and evaporated in vacuo to give a dark brown thick oil. The crude dark brown oil was purified by chromatography (hexane/ ethyl acetate; 80:20) to afford 0.2 g of 25 (7%) as a light cream solid. A single component was detected by TLC (hexane/ethyl acetate; 80:20) Rf, 0.5; NMR (CDCl3). δ4.8-5 (2H, d, CH2 --OH), d 7.4-8.4 (m, 5H, naphthyl). MS (HRFAB) (M+Li)+ calcd for C11H8OBrI, 368.8963 found 368.8978.

Provenance & Evidence