Hydrochloric Acid → 3-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-2-cyano-propionic acid ethyl ester

HRID 45487

反応式

HRID 45487 の反応式
[CH2:1]([O:3][C:4](=[O:16])[C:5]([C:14]#[N:15])=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)[CH3:2].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([Mg]Br)=[CH:20][CH:19]=1.Cl>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([C:14]#[N:15])[CH:6]([C:7]1[CH:8]=[CH:9][C:10]([Br:13])=[CH:11][CH:12]=1)[C:21]1[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=1)[CH3:2]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 367501Ethyl 3-(4-bromophenyl)-2-cyanoprop-2-enoateHCID 178478191HCID 178478191、化合物

生成物 1

HCID 576913973-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-2-cyano-propionic acid ethyl ester収率 91%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
85 °C

実験手順

A solution of 3-(4-bromo-phenyl)-2-cyano-acrylic acid ethyl ester (1.5 g, 5.36 mmol) in dry toluene (12 ml) was added dropwise to 4-chlorophenylmagnesium bromide (0.5 M solution in tetrahydrofuran, 6.96 ml, 6.96 mmol) at 0° C. The reaction mixture was heated to 85° C. for 3 hours, poured onto ice, acidified with 1N HCl and extracted with ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and concentrated, the crude product was purified over flash silica chromatography eluting with petroleum ether to ethyl acetate/petroleum ether (5:95) to afford the desired product (1.91 g, 91% yield). LC/MS: (PS-A2) Rt 3.78 [M+H]+ 391.93.

後処理

  1. additionpoured onto ice
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe crude product was purified over flash silica chromatography
  8. washeluting with petroleum ether to ethyl acetate/petroleum ether (5:95)

出典と根拠

ORDレコード
ord-c35a67d7d4624111bda5dd2070df42b2
出典データセット
uspto-grants-2013_09
特許番号
US08541461B2

関連ノート

読み込み中…