Iodine → HCID 67187010, compound

Temperature

50 °C

To a solution of 4-chloro-2-methoxy-phenylamine (600 mg, 3.81 mmol) in ethanol (12 ml) at 50° C. was added a solution of silver sulphate (2.14 g, 6.85 mmol) and iodine (967 mg, 3.81 mmol) in ethanol (8 ml). The resulting reaction mixture was stirred at 50° C. for 4 h. After cooling at 25° C., reaction mixture was filtered through a bed of celite and the filtrate was diluted with EtOAc (30 ml). The organic phase was washed with aqueous Na2S2O3 solution (2×15 ml), and brine (10 ml), dried over anhydrous Na2SO4, filtered, and evaporated off in vacuo. The crude residue was purified by flash column chromatography (2% EtOAc in hexane) to afford 4-chloro-2-iodo-6-methoxy-phenylamine (160 mg, 15%) as brown sticky liquid. GC-MS: 283 (M).

1. customThe resulting reaction mixture
2. temperatureAfter cooling at 25° C.
3. customreaction mixture
4. filtrationwas filtered through a bed of celite
5. additionthe filtrate was diluted with EtOAc (30 ml)
6. washThe organic phase was washed with aqueous Na2S2O3 solution (2×15 ml), and brine (10 ml)
7. dry with materialdried over anhydrous Na2SO4
8. filtrationfiltered
9. customevaporated off in vacuo
10. customThe crude residue was purified by flash column chromatography (2% EtOAc in hexane)

ORD record

ord-d6bd51a9c863445e929a6bf29d2fc73f

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199938B2