Reaction #806266

Reaction equation

α-bromo-2-nitro-p-tolunitrile

sodium formate

→

title compound

Yield 77.0%

α-Hydroxy-2-nitro-p-tolunitrile

Yield 77.0%

Solvents

CH2Cl2 EtOAc

ethanol water

Conditions

Workup

1. 1
   Temperaturewas refluxed for 2 h
2. 2
   Washwashed with H2O (3×)
3. 3
   Dryingdried (MgSO4)
4. 4
   Concentrationconcentrated
5. 5
   OtherPurification by flash chromatography (1,2 and 3% MeOH/CHCl3 gradient)

Procedure

A stirred solution containing α-bromo-2-nitro-p-tolunitrile (1.228 g, 5.095 mmol) and sodium formate (0.8664 g, 12.74 mmol) in ethanol:water (4:1, 25 mL) was refluxed for 2 h. The reaction was cooled to room temperature, diluted with 20% CH2Cl2/EtOAc, washed with H2O (3×), dried (MgSO4) and concentrated. Purification by flash chromatography (1,2 and 3% MeOH/CHCl3 gradient) gave 0.695 g (77%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 4.71 (d, 2H), 5.75 (t, 1H), 7.89 (dd, J=7.9 Hz, 1H), 8.14 (d, J=7.9 Hz, 1H), 8.32 (s, 1H).

Source