Nitric Acid → m-(Trifluoromethyl)nitrobenzene

Participants

Reaction Steps

To a stirred mixture of benzotrifluoride (80.0 g, 0.55 m) and concentrated sulphuric acid (200 ml) was added fuming nitric acid (95% w/w; 29.3 ml, 44.0 g, 1.2 equivalents) over 30 minutes, maintaining the temperature of the stirred reaction mixture at between 20° and 30° by means of external cooling. After completion of the addition, stirring was continued at room temperature for a further hour and then the reaction mixture was poured onto a mixture of ice (1 kg) and water (100 ml). The resultant mixture was extracted with dichloromethane (2×250 ml) and the combined extracts washed with water (2×100 ml). The organic solution was then dried (over MgSO4) and evaporated under reduced pressure at 30° to give 3-nitrobenzotrifluoride (102 g, 94.0% w/w by GLC assay, 91% yield), as a pale-yellow oil.

Provenance & Evidence