Triethylamine → 5-fluoro-1,3-dihydro-2H-indol-2-one

To a stirred solution of 11.1 g (0.1 mol) of 4-fluoroaniline in 200 ml of dichloromethane, at -60° to -65° C., was added, dropwise, a solution of 10.8 g (0.1 mol) of t-butyl hypochlorite in 25 ml of dichloromethane. Stirring was continued for 10 minutes at -60° to -65° C., and then was added, dropwise, a solution of 13.4 g (0.1 mol) of ethyl 2-(methylthio)acetate in 25 ml of dichloromethane. Stirring was continued at -60° C. for 1 hour and then was added, dropwise, at -60° to -65° C., a solution of 11.1 g (0.11 mol) of triethylamine in 25 ml of dichloromethane. The cooling bath was removed, and when the reaction mixture had warmed to room temperature, 100 ml of water was added. The phases were separated, and the organic phase was washed with saturated sodium chloride solution, dried (Na2SO4) and evaporated in vacuo. The residue was dissolved in 350 ml of diethyl ether, to which was added 40 ml of 2N hydrochloric acid. This mixture was stirred at room temperature overnight. The phases were separated and the ether phase was washed

1. additionwas added
2. stirringStirring
3. waitwas continued at -60° C. for 1 hour
4. additionwas added
5. customat -60° to -65° C.
6. customThe cooling bath was removed
7. addition100 ml of water was added
8. customThe phases were separated
9. washthe organic phase was washed with saturated sodium chloride solution
10. dry with materialdried (Na2SO4)
11. customevaporated in vacuo
12. dissolutionThe residue was dissolved in 350 ml of diethyl ether, to which
13. additionwas added 40 ml of 2N hydrochloric acid
14. stirringThis mixture was stirred at room temperature overnight
15. customThe phases were separated
16. washthe ether phase was washed

ORD record

ord-c9cb7180ca484dc2a9e18bd0059c37c7

Source dataset

uspto-grants-1987_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04658037