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

HRID 1428743

Reaction equation

[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]

Participants

Conditions

Temperature: 80 °C

Procedure

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%).

Workup

temperaturecooled to room temperature
filtrationThe mixture was filtered
dissolutionThe filtrate dissolved in ethyl acetate
extractionextracted with NaHCO3
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
customThe filtrate removed in vacuo
customThe crude was purified by column chromatography

Sources & evidence

ORD record: ord-be61a005c1f74ea6a7415c877677fe29
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937092B2

Linked notes

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