Reaction #2320144

Reaction equation

Al(CH3)3

2,3-dichlorobenzonitrile

azidotrimethylsilane

HCl

→

title compound

5-(2,3-dichlorophenyl)-1H-tetrazole

Solvents

toluene

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled to 0° C.
2. 2
   Temperatureto warm to ambient temperature
3. 3
   Extractionextracted twice with ethyl acetate (100 mL)
4. 4
   DryingThe combined organic phases were dried over Na2SO4
5. 5
   Filtrationfiltered through a ½″ pad of silica gel
6. 6
   Otherthe filtrate was evaporated under reduced pressure
7. 7
   OtherThe residue was purified by recrystallization from ethyl acetate/hexanes

Procedure

A 2.0 M solution of Al(CH3)3 in toluene (35 mL) was treated with 2,3-dichlorobenzonitrile (8.00 g, 37.2 mmol), azidotrimethylsilane (5.14 g, 44.6 mmol) slowly, and heated at 80° C. for 16 hours behind a blast shield. The mixture was cooled to 0° C. and treated with 2N HCl (100 mL) dropwise over 1 hour. The mixture was allowed to warm to ambient temperature and extracted twice with ethyl acetate (100 mL). The combined organic phases were dried over Na2SO4, filtered through a ½″ pad of silica gel, and the filtrate was evaporated under reduced pressure. The residue was purified by recrystallization from ethyl acetate/hexanes to provide the title compound. MS (DCI/NH3) m/z 215 (M)+; 1H NMR (DMSO-d6) δ 7.59 (t, 1H, J=8.0 Hz), 7.79 (dd, 1H, J=7.8, 1.7 Hz), 7.92 (dd, 1H, J=8.1, 1.7 Hz).

Source