Hydrochloric Acid → (2-Chloro-6-iodophenyl)methanol

関与物質

反応条件

反応手順

To a solution of 47.5 g (168 mmol) 2-chloro-6-iodo-benzoic acid in 300 ml tetrahydrofuran was added dropwise 420 ml (420 mmol) borane-tetrahydrofuran complex (1 M solution in tetrahydrofuran) over 30 min and then the reaction mixture was heated at 45° C. for 16 hours. 40 ml Methanol was added dropwise and then 70 ml of 25% aqueous hydrochloric acid was added dropwise, and the reaction mixture was heated at reflux for 2 hours. After cooling to room temperature the mixture was diluted with ethyl acetate and washed sequentially with water, saturated brine, 2 N aqueous sodium hydroxide solution, water and saturated brine. The organic phases was separated and dried over Na2SO4, filtered and concentrated in vacuo to afford a brown oil. The residue was taken up in 300 ml diethyl ether and the mixture was stirred for 10 min at 0° C. before being filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography (silica gel, ethyl acetate/heptane 1:3) to afford 8.17 g (18%) of the title compound as an orange crystalline solid. MS (EI): 270.0 (30%) & 268.0 (100%) (M+).

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