Hydrochloric Acid → Benzyl 2-cyano-2-(4-fluoro-5-methyl-2-nitrophenyl)acetate

HRID 73344

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5](F)=[CH:4][C:3]=1[CH3:12].[CH2:13]([O:20][C:21](=[O:25])[CH2:22][C:23]#[N:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH2:13]([O:20][C:21](=[O:25])[CH:22]([C:23]#[N:24])[C:5]1[CH:4]=[C:3]([CH3:12])[C:2]([F:1])=[CH:7][C:6]=1[N+:8]([O-:10])=[O:9])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 1,4-difluoro-2-methyl-5-nitrobenzene (1.00 g), cyanoacetic acid benzyl ester (1.01 g) and potassium carbonate (1.76 g) in N,N-dimethylformamide (20.0 mL) was stirred at 60° C. for 1 day. To this reaction mixture was added 1 mol/L hydrochloric acid (25.4 mL), and this mixture was extracted with diethyl ether. This organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure. This residue was washed with ethanol to give the title compound (1.54 g).

Workup

extractionthis mixture was extracted with diethyl ether
washThis organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customThe solvent was removed under reduced pressure
washThis residue was washed with ethanol

Sources & evidence

ORD record: ord-d523f99817fb4c26aa9722aefbfb32cf
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829040B2

Linked notes

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