反应详情

N-Iodosuccinimide (683 mg, 3.04 mmol) was added to a solution of 2-chloro-2′-fluoro-5-methoxybiphenyl (Preparation 96, 749 mg, 3.16 mmol) in concentrated sulfuric acid (0.09 mL), acetic acid (4.7 mL) and dichloromethane (4.7 mL). The resulting mixture was stirred at room temperature for 18 hours and then partitioned between dichloromethane (30 mL) and water (5 mL). The organic phase was separated and washed with water (2×5 mL), brine (5 mL), dried over MgSO4, filtered and evaporated to give a red oil. Column chromatography purification on silica, eluting with dichloromethane:heptanes (1:9) gave the title compound (671 mg, 58%) as a colourless oil.

1. custompartitioned between dichloromethane (30 mL) and water (5 mL)
2. customThe organic phase was separated
3. washwashed with water (2×5 mL), brine (5 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customevaporated
7. customto give a red oil
8. customColumn chromatography purification on silica
9. washeluting with dichloromethane:heptanes (1:9)