Sodium Iodide → 2-Cyclohexyloxy-1-iodoethane

To a solution of 2-cyclohexyloxyethyl 4-bromobenzenesulfonate (Preparation 86, 120 mg, 0.3 mmol) in acetone (5 ml) was added sodium iodide (90 mg, 0.6 mmol) and the reaction mixture was left to stir at room temperature for 18 h. A further equivalent of sodium iodide was added and the reaction mixture was stirred at room temperature for a further 18 h after which time the reaction mixture was heated to 80° C. for 5 h. The resulting precipitate was filtered and the filtrate was diluted with water (100 ml) and extracted with dichloromethane (100 ml). The extract was washed with brine (100 ml), dried (MgSO4) and concentrated in vacuo to give the title compound as a colourless oil (50 mg, 60%).

1. waitthe reaction mixture was left
2. stirringthe reaction mixture was stirred at room temperature for a further 18 h after which time the reaction mixture
3. temperaturewas heated to 80° C. for 5 h
4. filtrationThe resulting precipitate was filtered
5. additionthe filtrate was diluted with water (100 ml)
6. extractionextracted with dichloromethane (100 ml)
7. washThe extract was washed with brine (100 ml)
8. dry with materialdried (MgSO4)
9. concentrationconcentrated in vacuo

ORD record

ord-b9fca26f66f64c948eb834f60cbdddbf

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313312B1