N-bromobutanimide → 2-ethyl-5H-dibenzo[a,d]cyclohepten-5-one

HRID 596531Notes

Reaction equation

HRID 596531 reaction equation
CC1C=CC2C(=O)C3C=CC=CC=3CCC=2C=1.BrN1C(=O)CCC1=O.CC1C=CC2C(=O)C3C=CC=CC=3C=CC=2C=1.[CH2:43]([C:45]1[CH:60]=[CH:59][C:48]2[C:49](=[O:58])[C:50]3[CH:57]=[CH:56][CH:55]=[CH:54][C:51]=3[CH2:52][CH2:53][C:47]=2[CH:46]=1)[CH3:44]>C(Cl)(Cl)(Cl)Cl>[CH2:43]([C:45]1[CH:60]=[CH:59][C:48]2[C:49](=[O:58])[C:50]3[CH:57]=[CH:56][CH:55]=[CH:54][C:51]=3[CH:52]=[CH:53][C:47]=2[CH:46]=1)[CH3:44]

Participants

6

Reactant 4

HCID 67184N-bromobutanimideHCID 123988172-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-oneHCID 123988182-methyl-5H-dibenzo[a,d]cyclohepten-5-oneHCID 221172892-ethyl-10,11-dihydro-5H-dibenzo [a,d]cyclohepten-5-one

Product 1

HCID 200352582-ethyl-5H-dibenzo[a,d]cyclohepten-5-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

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 gm., 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.

Workup

  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 gm

Sources & evidence

ORD record
ord-6e71e1307d7a4dc09f653fced5cef57f
Source dataset
uspto-grants-1977_03
Patent number
US04011243

Reaction notes

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