Sodium Chloride → Methyl 2-Fluoro-4-nitrophenylacetate

HRID 1842953Notes

Reaction equation

HRID 1842953 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH:11](C(OC)=O)[C:12]([O:14][CH3:15])=[O:13].[Na+].[Cl-]>CS(C)=O.O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 53429620Dimethyl 2-(2-fluoro-4-nitrophenyl)malonate

Product 1

HCID 18369150Methyl 2-Fluoro-4-nitrophenylacetateYield 64%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

To a stirred solution of dimethyl 2-(2-fluoro-4-nitrophenyl)malonate (5.0 g, 18.5 mmol, 1.0 eq) in DMSO (30 mL) was added NaCl (1.07 g, 18.5 mmol, 1.0 eq) and water (0.5 mL) and stirred at 120° C. for 3 h. The reaction mixture was diluted with water (100 mL), extracted with EtOAc (50 mL×2), washed with brine, dried over Na2SO4 and the solvent evaporated. The crude residue was purified by CC using PE/EtOAc (19:1) to get methyl 2-(2-fluoro-4-nitrophenyl)acetate (2.5 g, 64%) as a viscous oil (TLC system: EtOAc/PE (1:4), Rf: 0.55).

Workup

  1. extractionextracted with EtOAc (50 mL×2)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customthe solvent evaporated
  5. customThe crude residue was purified by CC

Sources & evidence

ORD record
ord-229e1e62edc947fba1fd70c58aad648c
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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