Water → Ethyl 3-(2-bromo-6-chlorophenyl)propanoate

HRID 1471676ノート

反応式

HRID 1471676 の反応式
[Br:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[CH2:4][CH:5](C(OCC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].O.[Cl-].[Li+]>CS(C)=O>[Br:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

参加物

5

反応物 3

HCID 962Water2 回HCID 433294Lithium ChlorideHCID 67983387Diethyl 2-(2-bromo-6-chlorobenzyl)malonate

生成物 1

HCID 67982372Ethyl 3-(2-bromo-6-chlorophenyl)propanoate

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Diethyl 2-(2-bromo-6-chlorobenzyl)malonate (13.0 g, 35.7 mmol), water (1.29 mL, 71.5 mmol) and lithium chloride (3.03 g, 71.50 mmol) in dimethylsulfoxide (75 mL) were heated to +185° C. for 1 h. The solution was allowed to cool. 75 mL of water was added. The mixture was extracted with ethyl acetate. The organic phase was washed with water and aqueous NaHCO3. The organic phase was separated, dried over MgSO4, filtered and the solvent was removed by rotary evaporation to give the title compound. Yield: 7.34 g, 70%. 1H NMR (500 MHz, CDCl3) δ ppm 1.27-1.30 (m, 3H) 2.55-2.61 (m, 2H) 3.27-3.33 (m, 2H) 4.16-4.21 (m, 2H) 7.02 (t, 1H) 7.31-7.35 (m, 1H) 7.45-7.50 (m, 1H). MS m/z 293.0 [M+H]+.

後処理

  1. temperatureto cool
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with water and aqueous NaHCO3
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed by rotary evaporation

出典と根拠

ORDレコード
ord-bf30eeae73224437a1780998dc140f49
出典データセット
uspto-grants-2015_04
特許番号
US09012457B2

反応ノート

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