Iodine → 3-(4-Chlorophenyl)-1-iodopropane

To a solution of 1.55 g of 3 (4-chlorophenyl)propanol and 2.51 g of triphenylphosphine in 10 ml of N,N-dimethylformamide, there was gradually added dropwise at room temperature a solution of 2.42 g of iodine in 8 ml of N,N-dimethylformamide while confirming the consumption of iodine. When the color of the reaction mixture ceased to disappear any more, water was added to the reaction mixture, the excess iodine was reduced by addition of 5% aqueous sodium thiosulfate, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (20 g). Elution with hexane gave 1.82 g of 3-(4-chlorophenyl)propyl iodide.

1. customthe consumption of iodine
2. additionwas added to the reaction mixture
3. additionthe excess iodine was reduced by addition of 5% aqueous sodium thiosulfate
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with saturated aqueous solution of sodium chloride
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. washElution with hexane

ORD record

ord-0ed99ff5f3e34aa7a60a8e4d8d617bf3

Source dataset

uspto-grants-1991_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04987132