N-bromobutanimide → Ethyl 3-(3-bromo4-hydroxyphenyl)-2-phenoxypropionate

HRID 1860095ノート

反応式

HRID 1860095 の反応式
[Br:1]N1C(=O)CCC1=O.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][CH:11]=1>C(Cl)(Cl)Cl>[Br:1][C:15]1[CH:14]=[C:13]([CH2:16][CH:17]([O:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:12]=[CH:11][C:10]=1[OH:9]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 18625748Ethyl 3-(4-hydroxyphenyl)-2-phenoxypropionate

生成物 1

HCID 18625875Ethyl 3-(3-bromo4-hydroxyphenyl)-2-phenoxypropionate収率 77.3%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
70 °C

実験手順

N-bromosuccinimide (1.12 g) was added to a solution of ethyl 3-(4-hydroxyphenyl)-2-phenoxypropionate (1.43 g), which is the product of reference example 4(c) in chloroform (20 ml) at ambient temperature. The mixture was stirred at 70° C. for 4 hour and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified via chromatography on silica gel column using hexane/ethyl acetate=4/1 as the eluant to afford the desired compound (1.41 g) as a colorless oil.

後処理

  1. customat ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe ethyl acetate layer was separated
  5. washwashed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified via chromatography on silica gel column

出典と根拠

ORDレコード
ord-5bd58bb5f8344a2ab587f222083a1c02
出典データセット
uspto-grants-2003_03
特許番号
US06528525B1

反応ノート

読み込み中…