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

HRID 1576176노트

반응식

HRID 1576176 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-72e59ac1580f491e89174ddce609135d
출처 데이터셋
uspto-grants-1976_09
특허 번호
US03979430

반응 노트

불러오는 중…