4-Chloro-2-toluidine → 4-Chloro-2-iodo-6-methylaniline

Temperature

25 °C

To a solution of 4-chloro-2-methyl-phenylamine (1 g, 7.06 mmol) in acetic acid (20 ml) was added N-iodo succinimide (2.38 g, 10.59 mmol) portion wise at 25° C. under nitrogen. The reaction mixture was stirred at 25° C. for 16 h. The volatiles were removed in vacuo and the resultant crude residue was diluted with EtOAc (40 ml). The organic layer was washed with aqueous 1N NaOH solution (2×15 ml), followed by aqueous Na2S2O3 solution (2×15 ml), and brine (20 ml). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (5-10% EtOAc in hexane) to yield 4-chloro-2-iodo-6-methyl-phenylamine (1.5 g, 79%) as brown solid. GC-MS: 267 (M).

1. customThe volatiles were removed in vacuo
2. additionthe resultant crude residue was diluted with EtOAc (40 ml)
3. washThe organic layer was washed with aqueous 1N NaOH solution (2×15 ml)
4. dry with materialThe organic layer was dried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give a crude residue which
8. customwas purified by flash column chromatography (5-10% EtOAc in hexane)

ORD record

ord-de232dc04e55481c8747b4c1b1fbbe9a

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199938B2