Sodium Iodide → 1-Iodoethyl benzoate

Temperature

60 °C

1-Chloroethyl benzoate (6.30 g, 34.12 mmol) and sodium iodide (23.0 g, 153.56 mmol) were combined in acetonitrile (150 mL) and heated to 60° C. for 2 hours. The reaction mixture was concentrated under reduced pressure. Diethyl ether and dichloromethane were added to the residue and the solids were filtered off and the filtrate was concentrated under reduced pressure. After silica gel chromatography using ethyl acetate in hexanes the residue was combined with sodium iodide (4.70 g, 31.39 mmol) in acetonitrile (50 mL) and heated to 60° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure. Diethyl ether was added, the solids were filtered off and the filtrate was concentrated under reduced pressure. Chromatography on silica gel using ethyl acetate in hexanes provided 1-iodoethyl benzoate as a pale yellow oil (3.67 g, 39% yield).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionDiethyl ether and dichloromethane were added to the residue
3. filtrationthe solids were filtered off
4. concentrationthe filtrate was concentrated under reduced pressure
5. temperatureheated to 60° C. for 1.5 hours
6. concentrationThe reaction mixture was concentrated under reduced pressure
7. additionDiethyl ether was added
8. filtrationthe solids were filtered off
9. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-c63fee616cb24732876cd8747b864346

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859781B2