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

HRID 1460663ノート

反応式

HRID 1460663 の反応式
[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

参加物

7

反応物 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 54068354HCID 54068354、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 6344Dichloromethane溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-63ffd652700348989622f3c232281845
出典データセット
uspto-grants-1991_12
特許番号
US05071859

反応ノート

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