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

HRID 2226751ノート

反応式

HRID 2226751 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5b933255bb2e4ecc9b11762a0e3f51a5
出典データセット
uspto-grants-1994_09
特許番号
US05348965

反応ノート

読み込み中…