Reaction #8143

Reaction equation

i-butyl bromide

4-cyanophenol

triethylamine

→

4-iso-butoxybenzo-nitrile

Yield 85.6%

Solvents

water

DMF

Conditions

Workup

1. 1
   OtherThe resulting reaction mixture
2. 2
   TemperatureAfter cooling to room temperature
3. 3
   Extractionextracted with ethyl acetate (2×40 mL)
4. 4
   WashThe organic layer was washed with 4 M KOH (3×30 mL)
5. 5
   Dryingwith water, dried over Na2SO4
6. 6
   Concentrationconcentrated under vacuum

Procedure

To a solution of 4-cyanophenol (1.2 g, 10 mmol) in dry DMF (20 mL) was added triethylamine (20 mmol) followed by i-butyl bromide (2.7 g, 20 mmol). The resulting reaction mixture was stirred at 100° C. for 6 h. After cooling to room temperature, the reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (2×40 mL). The organic layer was washed with 4 M KOH (3×30 mL) and then with water, dried over Na2SO4 and concentrated under vacuum to provide 1.5 g (85%) 4-iso-butoxybenzo-nitrile that was used for the next step without further purification. 1H NMR (DMSO-D6): δ 0.95 (d, 6H, 2CH3), 2.0 (m, 1H, CH(CH3)2), 3.8 (d, 2H, CH2), 7.4 (AA′BB′, Δ=20 Hz, 4H, Ar).

Source