N-bromobutanimide → 2-(alpha-bromoethyl)-5H-dibenzo[a,d]cyclohepten-5-one

HRID 596532Notes

Reaction equation

HRID 596532 reaction equation
[CH3:1]C1C=CC2C(=O)C3C=CC=CC=3C=CC=2C=1.BrN1C(=O)CCC1=O.[Br:26][CH2:27][C:28]1[CH:43]=[CH:42][C:31]2[C:32](=[O:41])[C:33]3[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=3[CH:35]=[CH:36][C:30]=2[CH:29]=1.C(C1C=CC2C(=O)C3C=CC=CC=3C=CC=2C=1)C>C(Cl)(Cl)(Cl)Cl>[Br:26][CH:27]([C:28]1[CH:43]=[CH:42][C:31]2[C:32](=[O:41])[C:33]3[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=3[CH:35]=[CH:36][C:30]=2[CH:29]=1)[CH3:1]

Participants

6

Reactant 4

HCID 67184N-bromobutanimideHCID 123988182-methyl-5H-dibenzo[a,d]cyclohepten-5-oneHCID 123988192-bromomethyl-5H-dibenzo[a,d]cyclohepten-5-oneHCID 200352582-ethyl-5H-dibenzo[a,d]cyclohepten-5-one

Product 1

HCID 214031032-(alpha-bromoethyl)-5H-dibenzo[a,d]cyclohepten-5-oneYield 80%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

39.7 Gm. of 2-methyl-5H-dibenzo[a,d]cyclohepten-5-one is refluxed in 1200 ml. of carbon tetrachloride with 35.2 gm. of N-bromosuccinimide for 14 hours, irradiating with a 100 watt incandescent lamp. The solution is cooled, filtered and evaporated. The residue is recrystallized from methylene chloride/hexane to afford 27.3 gm., 51%, of 2-bromomethyl-5H-dibenzo[a,d]cyclohepten-5-one, m.p. 128°-132° C. Use of 2-ethyl-5H-dibenzo[a,d]cyclohepten-5-one gives 80% of 2-(α-bromoethyl)-5H-dibenzo[a,d]cyclohepten-5-one, m.p. 93°-95° C.

Workup

  1. customirradiating with a 100 watt incandescent lamp
  2. temperatureThe solution is cooled
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is recrystallized from methylene chloride/hexane
  6. customto afford 27.3 gm

Sources & evidence

ORD record
ord-ec55082124594a5d9b5eb739605d6982
Source dataset
uspto-grants-1977_03
Patent number
US04011243

Reaction notes

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