Reaktion #84240

Reaktionsgleichung

N-iodosuccinimide

4-Amino-2-trifluoromethyl-benzonitrile

p-toluenesulfonic acid monohydrate

methanol

→

title compound

4-Amino-5-iodo-2-trifluoromethyl-benzonitrile

Lösungsmittel

THF

aluminium

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGwhile the solution was stirred for 20 min.
2. 2
   workup.STIRRINGto stir overnight (16 hrs)
3. 3
   EinengenThe reaction mixture was concentrated in vacuo
4. 4
   Sonstigetriturated with hexanes (3×400 mL)
5. 5
   Einengenconcentrated to dryness
6. 6
   workup.DISSOLUTIONThe crude solid was dissolved in diethyl ether (400 mL)
7. 7
   Waschenwashed with water (3×)
8. 8
   workup.ADDITIONthe organic extracts were diluted with hexanes (400 mL)
9. 9
   Sonstigea white solid precipitated
10. 10
    FiltrationThe solid was filtered
11. 11
    Sonstigedried in a vacuum oven (35° C. @ 762 Torr) overnight

Vorschrift

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.

Quelle