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

HRID 1258200Notes

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-34ce3cbf77a44f06855ba2e5c4e69404
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466152B2

Reaction notes

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