反应详情

温度

80 °C

60.5 Gm. of 2-methyl-10,11-dihydro-5H-dibenzo[a,d] cyclohepten-5-one is refluxed in 500 ml. of carbon tetrachloride with 58.2 gm. of N-bromosuccinimide for 8 hours. The solution is cooled and filtered and the solvent removed under vacuum. The residue is dissolved in 200 ml. of dimethylformamide and 44 gm. of 1,5-diazabicyclo[3.4.0]nonene-5 is added. The mixture is heated to 80°C. for 20 minutes, then cooled and added to water. The solution is extracted with ether and the extract washed, dried and evaporated. The residue is recrystallized from acetone/hexane to afford 39.7 g., 69% of 2-methyl-5H-dibenzo[a,d]cyclohepten-5-one, m.p. 78°-80°C. Use of 2-ethyl-10,11-dihydro-5H-dibenzo [a,d]cyclohepten-5-one gives a similar yield of 2-ethyl-5H-dibenzo[a,d]cyclohepten-5-one, m.p. 62°-64°C.

1. temperatureThe solution is cooled
2. filtrationfiltered
3. customthe solvent removed under vacuum
4. dissolutionThe residue is dissolved in 200 ml
5. additionof 1,5-diazabicyclo[3.4.0]nonene-5 is added
6. temperaturecooled
7. additionadded to water
8. extractionThe solution is extracted with ether
9. washthe extract washed
10. customdried
11. customevaporated
12. customThe residue is recrystallized from acetone/hexane
13. customto afford 39.7 g