Methanol → 4-Amino-5-iodo-2-(trifluoromethyl)benzonitrile

4-Amino-2-trifluoromethyl-benzonitrile (20.44 g, 109.79 mmoles) and p-toluenesulfonic acid monohydrate (1.05 g, 5.52 mmoles) were dissolved methanol (200 mL) and THF (200 mL), and the reaction mixture was stirred under a nitrogen atmosphere. The reaction vessel was wrapped in aluminium foil, while the solution was stirred for 20 min., then N-iodosuccinimide (30.41 g, 135.17 mmoles) was added and the reaction was allowed to stir overnight (16 hrs). The reaction mixture was concentrated in vacuo, triturated with hexanes (3×400 mL) and concentrated to dryness. The crude solid was dissolved in diethyl ether (400 mL), washed with water (3×), the organic extracts were diluted with hexanes (400 mL) and a white solid precipitated. The solid was filtered and dried in a vacuum oven (35° C. @762 Torr) overnight to yield the title compound.

1. stirringwhile the solution was stirred for 20 min.
2. stirringto stir overnight (16 hrs)
3. concentrationThe reaction mixture was concentrated in vacuo
4. customtriturated with hexanes (3×400 mL)
5. concentrationconcentrated to dryness
6. dissolutionThe crude solid was dissolved in diethyl ether (400 mL)
7. washwashed with water (3×)
8. additionthe organic extracts were diluted with hexanes (400 mL)
9. customa white solid precipitated
10. filtrationThe solid was filtered
11. customdried in a vacuum oven (35° C. @762 Torr) overnight

ORDレコード

ord-1fd312ac805b4dfeadac16093750d1c8

出典データセット

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07427682B2