Reaction #74967

Reaction equation

benzoquinone

1,2,3,4,5,5-hexabromo-1,3-cyclopentadiene

→

1,2,3,4,9,9-hexabromo-1,4-dihydro-1,4-methanonaphthalene-5,8-diol

Solvents

toluene

Conditions

Workup

1. 1
   Temperatureto reflux temperature
2. 2
   Temperaturerefluxed for four hours
3. 3
   OtherAt the end of this reaction period a dark solid
4. 4
   Otherhad formed
5. 5
   Washwashed with Skelly B solvent
6. 6
   OtherThe solid was then recrystallized from benzene
7. 7
   Otherwhite crystals were obtained

Procedure

A mixture of benzoquinone, 10.8 g. toluene (40 ml) and 1,2,3,4,5,5-hexabromo-1,3-cyclopentadiene (60 g.) was heated to reflux temperature and refluxed for four hours. At the end of this reaction period a dark solid had formed. This solid was placed on a Buchner funnel and washed with Skelly B solvent and a small amount of methanol. The solid was then recrystallized from benzene and white crystals were obtained, m.p. 204°-206° C.

Source