Reaction #939040

Reaction equation

Isobutyl bromide

methyl 4-hydroxy-3-nitrobenzoate

potassium carbonate

→

desired compound

Yield 87.3%

Methyl 4-isobutyloxy-3-nitrobenzoate

Yield 87.3%

Solvents

DMF

Conditions

Workup

1. 1
   Temperaturecooled to room temperature
2. 2
   FiltrationThe precipitated crystalline product was collected by filtration
3. 3
   Washwashed with water (50 mL)
4. 4
   Otherdried for 30 min in air
5. 5
   WashThe dried crystalline product was then washed with hexane (40 mL)
6. 6
   Otherdried in air

Procedure

Isobutyl bromide (10.5 mL, 95.8 mmol) was added to a suspension of methyl 4-hydroxy-3-nitrobenzoate (6.26 g, 31.8 mmol) and potassium carbonate (13.2 g, 95.5 mmol) in dry DMF (40 mL). The resulting mixture was stirred at 90° C. for 44 hours and then cooled to room temperature. Subsequently, ice-water (80 mL) was added to the cooled mixture. The precipitated crystalline product was collected by filtration, washed with water (50 mL), and dried for 30 min in air. The dried crystalline product was then washed with hexane (40 mL), and dried in air to give 7.03 g (yield 87%) of the desired compound in the form of a pale orange crystalline product.

Source