Iodine → 2-Fluoro-6-iodo-4-methylaniline

A solution of 2-fluoro-4-methylphenylamine (1.25 g, 10 mmol) in 5 mL of methanol was treated with a solution of iodine (1.27 g, 5 mmol) in a mixture of 25 mL of methanol and 3 mL of hydrogen peroxide over a period of 15 minutes at room temperature. After 18 hours, the reaction mixture was quenched with 30 mL of saturated aqueous sodium thiosulfate and extracted with three 50 mL portions of dichloromethane. The combined organic layers were washed with two 30 mL portions of saturated sodium bisulfite solution, three 50 mL portions of water, dried over sodium sulfate, and concentrated in vacuo. Chromatography on SiO2 (10% ethyl acetate in hexanes) gave 1.1 g of the title product as a light brownish oil (44% yield).

1. customthe reaction mixture was quenched with 30 mL of saturated aqueous sodium thiosulfate
2. extractionextracted with three 50 mL portions of dichloromethane
3. washThe combined organic layers were washed with two 30 mL portions of saturated sodium bisulfite solution, three 50 mL portions of water
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated in vacuo

ORD record

ord-f2188e324455469d907cc77fb48a578e

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741897B2