Hydrochloric Acid → HCID 86654323, 화합물

HRID 888565

반응식

HRID 888565 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)=[CH:9][CH:8]=1)[CH3:2].ClC1C=CC([Mg][Br:25])=CC=1.[ClH:26].[C:27]1(C)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:1]([O:3][C:4](=[O:16])[C:5]([C:30]1[CH:31]=[CH:32][C:27]([Br:25])=[CH:28][CH:29]=1)([C:14]#[N:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:26])=[CH:9][CH:8]=1)[CH3:2]

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 367501Ethyl 3-(4-bromophenyl)-2-cyanoprop-2-enoateHCID 178478191HCID 178478191, 화합물

생성물 1

HCID 86654323HCID 86654323, 화합물수율 91%

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-3e3e21ab170d41c7a5c51f7e0b7c237d
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247576B2

연결된 노트

불러오는 중…