反应详情

温度

45 °C

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+).

1. temperaturethe reaction mixture was heated
2. temperatureat reflux for 2 hours
3. temperatureAfter cooling to room temperature the mixture
4. washwashed sequentially with water, saturated brine, 2 N aqueous sodium hydroxide solution, water and saturated brine
5. customThe organic phases was separated
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto afford a brown oil
10. filtrationbefore being filtered
11. concentrationThe filtrate was concentrated in vacuo
12. customthe residue was purified by chromatography (silica gel, ethyl acetate/heptane 1:3)