反应详情

5-Chloro-2-fluoro-benzenesulfonyl chloride (10.5 g) and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (10.0 g) were added to a reaction vessel containing a magnetic stirring bar, followed by 200 ml dry DCM and 4.1 ml pyridine. The reaction mixture was stirred at RT for 20 h before being cooled on an ice-bath and quenched with 1M aqueous sodium hydroxide solution. The organic phase was separated and the aqueous phase acidified with 2M aqueous hydrochloric acid and extracted three times with EtOAc. The combined organic phases were washed with brine and dried over sodium sulfate and evaporated to afford the crude product. Purification by flash chromatography on silica gel using a mixture of EtOAc and heptane as the eluent afforded the title compound as a colorless solid after evaporation of the solvents under reduced pressure. Yield: 14.14 g (75%).

1. additioncontaining a magnetic stirring bar
2. temperaturebefore being cooled on an ice-bath
3. customquenched with 1M aqueous sodium hydroxide solution
4. customThe organic phase was separated
5. extractionextracted three times with EtOAc
6. washThe combined organic phases were washed with brine
7. dry with materialdried over sodium sulfate
8. customevaporated
9. customto afford the crude product
10. customPurification by flash chromatography on silica gel using
11. additiona mixture of EtOAc and heptane as the eluent