Sulfuric Acid → HCID 118622806, compound

HRID 2202313Notes

Reaction equation

HRID 2202313 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([F:11])[C:3]=1[CH2:12][C:13]([OH:15])=[O:14].S(=O)(=O)(O)O.[C:21](=O)([O-])O.[Na+].C(OCC)(=O)C>CO.O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([F:11])[C:3]=1[CH2:12][C:13]([O:15][CH3:21])=[O:14]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 698373442-(2,6-difluoro-4-nitrophenyl)acetic acid

Product 1

HCID 118622806HCID 118622806, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-(2,6-difluoro-4-nitrophenyl)acetic acid (27.90 g, 128.5 mmol) and conc. sulfuric acid (1.0 mL) in MeOH (260 mL) was heated under reflux for 18 hr. The reaction mixture was neutralized with aqueous sodium hydrogencarbonate solution, and ethyl acetate and water were added thereto. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 0→100% ethyl acetate/hexane) to give methyl 2-(2,6-difluoro-4-nitrophenyl)acetate (28.71 g, 128.5 mmol, 97.0%) as a yellow solid.

Workup

  1. temperatureunder reflux for 18 hr
  2. additionwere added
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 0→100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-63d0aa91c5c54c729def52e9193936e8
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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