4-(Trifluoromethyl)aniline → 2-Iodo-4-(trifluoromethyl)aniline

To a solution of 4-(trifluoromethyl)benzenamine (10.0 g, 0.0617 mol) in dry methanol (200 ml) was added iodine monochloride (10.49 g, 0.148 mol) in dry MDC (40 ml) at RT slowly. Reaction mixture was stirred at RT over night. The reaction mixture was concentrated, water was added and extracted with ethyl acetate (2×100 ml). The organic layer was washed with water, brine (2×50 ml), dried over Na2SO4 and concentrated. The crude product was purified by column chromatography using 6% ethyl acetate in pet-ether to get 2-iodo-4-(trifluoromethyl)benzenamine (12.5 g, 70%) as pale yellow liquid. 1H NMR (400 MHz, CDCl3) δ 4.42 (bs, 2H), 6.75 (d, 1H), 7.38 (d, 1H), 7.87 (s, 1H).

1. customReaction mixture
2. concentrationThe reaction mixture was concentrated
3. additionwater was added
4. extractionextracted with ethyl acetate (2×100 ml)
5. washThe organic layer was washed with water, brine (2×50 ml)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customThe crude product was purified by column chromatography

ORD record

ord-f6286e69485a487db77edc1dd4f8161a

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07829571B2