Reaction #69006

Reaction equation

4-fluoro-1-nitrobenzene

3-methyl-1H-1,2,4-triazole

K2CO3

DMF

→

3-methyl-1-(4-nitrophenyl)-1H-1,2,4-triazole

Solvents

water

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled down to room temperature
2. 2
   Extractionextracted with EtOAc (3×)
3. 3
   DryingThe organic solution was dried over anhydrous MgSO4
4. 4
   Concentrationconcentrated in vacuo
5. 5
   Otherto provide a solid
6. 6
   OtherPurification of this material by column chromatography on silica gel (40% EtOAc/hexane)

Procedure

A mixture of 4-fluoro-1-nitrobenzene (0.28 g, 2.0 mmol), 3-methyl-1H-1,2,4-triazole (0.18 g, 2.2 mmol), K2CO3 (0.55 g, 4.0 mmol) and DMF (2 mL) was heated at 70° C. overnight. The reaction mixture was cooled down to room temperature, diluted with water, extracted with EtOAc (3×). The organic solution was dried over anhydrous MgSO4 and concentrated in vacuo to provide a solid. Purification of this material by column chromatography on silica gel (40% EtOAc/hexane) provided 3-methyl-1-(4-nitrophenyl)-1H-1,2,4-triazole as the major product. 1H NMR (CDCl3, 400 MHz) δ 8.59 (s, 1H), 8.39 (d, 2H), 7.88 (d, 2H), 2.53 (s, 3H). Further elution with 65% EtOAc/hexane provided 5-methyl-1-(4-nitrophenyl)-1H-1,2,4-triazole as the minor product. 1H NMR (CDCl3, 400 MHz) δ 8.34 (d, 2H), 7.93 (s, 1H), 7.66 (d, 2H), 2.59 (s, 3H).

Source