Reaction #7051

Reaction equation

bromoacetonitrile

7-hydroxy-1H-indole

potassium carbonate

→

(1H-Indol-7-yloxy)-acetonitrile

Solvents

acetonitrile

Conditions

Workup

1. 1
   OtherIn a 100 mL roundbottom flask equipped with a magnetic stirrer
2. 2
   Temperatureto warm to ambient temperature
3. 3
   workup.STIRRINGstirring
4. 4
   WashThe solution was washed with water (2×30 mL) and brine (1×30 mL)
5. 5
   Dryingdried over MgSO4
6. 6
   Concentrationconcentrated in vacuo
7. 7
   OtherThe resulting oily brown residue was purified by flash chromatography (95:5 ethyl acetate:hexanes to 85:15 ethyl acetate:hexanes over minutes)

Procedure

In a 100 mL roundbottom flask equipped with a magnetic stirrer and rubber septum, 7-hydroxy-1H-indole (1.66 g., 12.48 mmol) was dissolved 50 mL anhydrous acetonitrile. The flask was charged with potassium carbonate (6.88 g., 49.9 mmol) and cooled to 0° C. While stirring, bromoacetonitrile (1.64 g., 13.73 mmol) was added dropwise over two minutes. The reaction mixture was allowed to warm to ambient temperature and stirring was continued for three hours. The solution was washed with water (2×30 mL) and brine (1×30 mL), dried over MgSO4 and concentrated in vacuo. The resulting oily brown residue was purified by flash chromatography (95:5 ethyl acetate:hexanes to 85:15 ethyl acetate:hexanes over minutes) to give (1H-Indol-7-yloxy)-acetonitrile as a crystalline solid (0.244-g.) ms: (M−H)−=171.2.

Source