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

HRID 881613

Reaction equation

HRID 881613 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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2306581,4-Difluoro-2-methyl-5-nitrobenzeneHCID 560818Benzyl 2-cyanoacetate

Product 1

HCID 58437495Benzyl 2-cyano-2-(4-fluoro-5-methyl-2-nitrophenyl)acetateYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. extractionthis mixture was extracted with diethyl ether
  2. washThis organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure
  6. washThis residue was washed with ethanol

Sources & evidence

ORD record
ord-0e84a413efe6400cac12a9b7e5204e6a
Source dataset
uspto-grants-2015_03
Patent number
US08993616B2

Linked notes

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