Réaction #558760

Équation de réaction

2,6-dinitrobenzonitrile

sodium

n-propanol

→

2-nitro-6-propoxybenzonitrile

Rendement 77.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONaddition
2. 2
   Filtrationthe precipitate was collected by filtration
3. 3
   Autredried

Mode opératoire

To a solution of 2,6-dinitrobenzonitrile (6 g, 31.07 mmol) in dry DMF (45 mL) at 0° C., was added a solution of sodium (815 mg, 35.42 mmol) in n-propanol (23.5 mL) dropwise over 30 minutes. After compete addition, the reaction mixture was warmed to room temperature and stirred for 2.5 hours. The reaction was poured into an ice/water mixture (250 mL), and the precipitate was collected by filtration and dried to yield 2-nitro-6-propoxybenzonitrile (4.95 g, 77%) as a light brown solid. 1H NMR (400 MHz, CDCl3) δ 1.11 (d, J=7.5 Hz, 3H), 1.93 (sext, J=7.5 Hz, 2H), 4.14 (t, J=7.0 Hz, 2H), 7.31 (d, J=8.6 Hz, 1H), 7.69 (t, J=8.6 Hz, 1H), 7.82 (d, J=8.6 Hz, 1H).

Source