Hydrogen Bromide → [4-({4-Bromo-2-[(2-hydroxyethoxy)methyl]phenyl}amino)-2-chlorophenyl](2-methylphenyl)methanone

HRID 1797304ノート

反応式

HRID 1797304 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][O:16][CH2:17][CH2:18][OH:19])[CH:5]=[CH:4][C:3]=1[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:28])=[O:21].[BrH:29].[OH-].[Na+]>CS(C)=O>[Br:29][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6]2[CH:5]=[CH:4][C:3]([C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])=[O:21])=[C:2]([Cl:1])[CH:7]=2)=[C:10]([CH2:15][O:16][CH2:17][CH2:18][OH:19])[CH:11]=1

参加物

5

反応物 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 10294143[2-Chloro-4-({2-[(hydroxyethoxy)methyl]phenyl}amino)phenyl](2-methylphenyl)methanone

生成物 1

HCID 10227340[4-({4-Bromo-2-[(2-hydroxyethoxy)methyl]phenyl}amino)-2-chlorophenyl](2-methylphenyl)methanone

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Compound 156 (3.8 g, 9.6 mmol) was dissolved in DMSO (115 mL). The solution was cooled on an ice bath and 48% aqueous HBr (32 mL, 285 mmol) was added slowly. The solution was stirred in a closed vessel at room temperature for 5 days. The reaction mixture was cooled on an ice bath and 27% aqueous NaOH (30 mL) was added to give a basic solution. The water phase was extracted three times with EtOAc, the combined organic phases were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by flash chromatography using EtOAc/petroleum ether 1:1 as the eluent to afford the title compound as a slightly coloured crystalline compound.

後処理

  1. temperatureThe solution was cooled on an ice bath
  2. temperatureThe reaction mixture was cooled on an ice bath
  3. customto give a basic solution
  4. extractionThe water phase was extracted three times with EtOAc
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-00e0f76388c34fc7be24405c40a4aa4b
出典データセット
uspto-grants-2006_04
特許番号
US07034015B2

反応ノート

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