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

HRID 1428743

反応式

HRID 1428743 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-be61a005c1f74ea6a7415c877677fe29
出典データセット
uspto-grants-2015_01
特許番号
US08937092B2

関連ノート

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