1,2-Dibromoethane → 1-[2-(2-Bromoethoxy)-1-(3-fluorophenyl)ethenyl]-3-fluorobenzene

HRID 1460663노트

반응식

HRID 1460663 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[Br:20][CH2:21][CH2:22]Br>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+].O>[Br:20][CH2:21][CH2:22][O:10][CH:9]=[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

참가 물질

7

반응물 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 54068354HCID 54068354, 화합물

생성물 1

HCID 106884311-[2-(2-Bromoethoxy)-1-(3-fluorophenyl)ethenyl]-3-fluorobenzene수율 95%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 6344Dichloromethane용매2회HCID 57417360Sodium chloride; water용매

실험 절차

bis(3-Fluorophenyl)acetaldehyde (4.82 g, 0.0208 mol) was dissolved in dichloromethane (50 ml) and tetra-n-butyl ammonium bromide (0.67 g, 0.00208 mol) was added. 12N sodium hydroxide solution (50 ml) and 1,2-dibromoethane (17.9 ml, 0.208 mol) Were introduced and the mixture was stirred vigorously at room temperature for 20 h. Dichloromethane (100 ml) and saturated brine (50 ml) were added, and the phases were separated. The aqueous phase was extracted further with dichloromethane (50 ml) and the combined dichloromethane extracts were washed with water (2×75 ml) and saturated brine (50 ml). Drying of the dichloromethane solution (Na2SO4) and evaporation provided the title compound as an oil (6.66 g, 95%), TLC rf 0.71 (SiO2 : dichloromethane).

후처리

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted further with dichloromethane (50 ml)
  3. washthe combined dichloromethane extracts were washed with water (2×75 ml) and saturated brine (50 ml)
  4. dry with materialDrying of the dichloromethane solution (Na2SO4) and evaporation

출처 및 근거

ORD 기록
ord-63ffd652700348989622f3c232281845
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05071859

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