Potassium Iodide → HCID 15572233, compound

Participants

Reaction Steps

Combine 2,6-dimethyl-4-(tetrafluoro-1,3-dichloro-2-hydroxy-2-propyl)aniline [Gilbert, et. al., J. Org. Chem., 30, 1001 (1965)] (26 g=0.08 mol) with ethyl bromoacetate (22 g=0.13 mol) and potassium iodide (22 g=0.13 mol) in 150 ml CH3CN. Heat to reflux and add NaHCO3 (13.4 g=0.16 mol). Heat at reflux 20 hours, allow to cool, pour onto water, and extract with Et2O. Wash the Et2O with 10% Na2CO3, then 1 N HCl. Dry over MgSO4 and filter. Add 4 N HCl/Et2O and dilute with an equal volume of hexane. Decant and wash the solid with benzene. Partition the solid between 10% Na2CO3 and Et2O. Dry and concentrate the Et2O. Recrystallize the residue from hexane to obtain the title product as a white solid, melting at about 102°-104° C.

Provenance & Evidence