Dimethylformamide → Methyl 2-(3-chloro-4-cyanophenyl)acetate

HRID 1428743

반응식

HRID 1428743 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:5]=[CH:6][C:7]=1OS(C(F)(F)F)(=O)=O.[CH3:21][N:22](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:5]=[CH:6][C:7]=1[C:21]#[N:22]

참가 물질

6

반응물 2

HCID 6228DimethylformamideHCID 3564187Methyl 2-[3-chloro-4-(trifluoromethylsulfonyloxy)phenyl]acetate

생성물 1

HCID 3564186Methyl 2-(3-chloro-4-cyanophenyl)acetate수율 37%

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

To a stirred solution of methyl 2-(3-chloro-4-(trifluoromethylsulfonyloxy)-phenyl)acetate (4.419 g, 13.283 mmol) in dimethylformamide were added zinc cyanide (1.6 g, 13.681 mmol) and tetrakis(triphenylphosphine) palladium (1.5 g, 1.3283 mmol). The reaction mixture was stirred for 34 h at 80° C., then cooled to room temperature and diluted with ethyl acetate. The mixture was filtered using celite pad. The filtrate dissolved in ethyl acetate and extracted with NaHCO3. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to give methyl 2-(3-chloro-4-cyanophenyl)acetate (1.044 g, 37%).

후처리

  1. temperaturecooled to room temperature
  2. filtrationThe mixture was filtered
  3. dissolutionThe filtrate dissolved in ethyl acetate
  4. extractionextracted with NaHCO3
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate removed in vacuo
  8. customThe crude was purified by column chromatography

출처 및 근거

ORD 기록
ord-be61a005c1f74ea6a7415c877677fe29
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937092B2

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