Reaction #792196

Reaction equation

2-diazo-1-(thiophen-2-yl)ethanone

3,4,5,6-tetrachlorocyclohexa-3,5-diene-1,2-dione

→

(4,5,6,7-tetrachlorobenzo[d][1,3]dioxol-2-yl)(thiophen-2-yl)methanone

Yield 43.7%

Solvents

benzene

Conditions

Workup

1. 1
   Temperaturerefluxed vigorously for 6 hours
2. 2
   OtherThe solvent was then evaporated to dryness
3. 3
   OtherEvaporation of the solvent

Procedure

2-diazo-1-(thiophen-2-yl)ethanone (2.3 g, 0.0151 mol) and 3,4,5,6-tetrachlorocyclohexa-3,5-diene-1,2-dione (3.36 g, 0.0136 mol) were then combined in dry benzene (25 mL) and refluxed vigorously for 6 hours. The solvent was then evaporated to dryness, and the crude material was subjected to column chromatography using 100-200 mesh silica gel and 15% ethyl acetate-hexane solvent system. Evaporation of the solvent yielded (4,5,6,7-tetrachlorobenzo[d][1,3]dioxol-2-yl)(thiophen-2-yl)methanone as an orange solid (2.2 g, 43.4%).

Source