1,2-Dibromoethane → 2-((10, 11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)methoxy)ethylbromide

HRID 2226751노트

반응식

HRID 2226751 반응식
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH:16]=[O:17])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:18][CH2:19][CH2:20]Br.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][O:17][CH2:20][CH2:19][Br:18])[C:5]=2[CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 1495090410,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-carboxaldehyde

생성물 1

HCID 109695372-((10, 11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)methoxy)ethylbromide

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-carboxaldehyde (11.3 g, 51 mmol, prepared in a similar way as described in Acta Chem. Scand. 1978, B33, 100-103) and tetrabutylammonium bromide (1.64 g, 5.1 mmol) in dichloromethane (100 ml) was added 1,2-dibromoethane (62 ml) and a 12 M sodium hydroxide solution (100 ml). The reaction mixture was stirred vigorously overnight and dichloromethane (100 ml) was added. The phases were separated and the aqueous phase was extracted with dichloromethane (100 ml). The combined organic phases were washed with a 0.2 M hydrochloric acid solution (100 ml), brine (25 ml) and dried over magnesium sulphate. The solvent was evaporated in vacuo to give 14.1 g of 2-((10, 11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)methoxy)ethylbromide. TLC: rf=0.48 (SiO2 ; ethyl acetate/n-heptane=1:4).

후처리

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with dichloromethane (100 ml)
  3. washThe combined organic phases were washed with a 0.2 M hydrochloric acid solution (100 ml), brine (25 ml)
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was evaporated in vacuo

출처 및 근거

ORD 기록
ord-5b933255bb2e4ecc9b11762a0e3f51a5
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05348965

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