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

HRID 924695

반응식

HRID 924695 반응식
[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]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 367501Ethyl 3-(4-bromophenyl)-2-cyanoprop-2-enoateHCID 178478191HCID 178478191, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
85 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f497e6a10d5c43e082e71cb6fb6049a2
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09283226B2

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