Reaction #360313

Reaction equation

3-Chloro-benzoic acid hydrazide

2-bromo-1,1,1-triethoxypropane

→

2-(1-bromo-ethyl)-5-(3-chloro-phenyl)-[1,3,4]oxadiazole

Yield 32.0%

Conditions

Workup

1. 1
   Otherpurified
2. 2
   OtherThe product was re-purified by flash column chromatography
3. 3
   workup.ADDITIONa mixture of ethyl acetate:hexanes:dichloromethane (1:19:20)

Procedure

3-Chloro-benzoic acid hydrazide (170 mg, 1 mmol) and 2-bromo-1,1,1-triethoxypropane (1 ml) were heated in a sealed vial at 120° C. for 10 min. The reaction mixture was place directly onto a flash column (silica gel) and purified using 0-50% dichloromethane in hexanes. The product was re-purified by flash column chromatography using a mixture of ethyl acetate:hexanes:dichloromethane (1:19:20) to afford 2-(1-bromo-ethyl)-5-(3-chloro-phenyl)-[1,3,4]oxadiazole (93 mg, 32%, colorless oil). 1H NMR (CDCl3) d (ppm): 8.09 (t, 1H), 7.99 (t, 1H), 7.55 (m, 3H), 5.30 (m, 1H), 2.21 (q, 3H).

Source