Ethanol → Ethyl 2-(4-fluoro-2-methyl-5-nitrophenyl)acetate

HRID 1257178Notes

Reaction equation

HRID 1257178 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH2:11][C:12]([OH:14])=[O:13])=[C:4]([CH3:15])[CH:3]=1.OS(O)(=O)=O.[CH3:21][CH2:22]O>>[F:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH2:11][C:12]([O:14][CH2:21][CH3:22])=[O:13])=[C:4]([CH3:15])[CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 690381782-(4-Fluoro-2-methyl-5-nitrophenyl)acetic acid

Product 1

HCID 68983461Ethyl 2-(4-fluoro-2-methyl-5-nitrophenyl)acetateYield 81%

Conditions

Temperature
85 °C

Procedure

2-(4-Fluoro-2-methyl-5-nitrophenyl)acetic acid (18.43 g, 86.5 mmol) and conc. H2SO4 (4.00 mL) were combined in EtOH (300 mL) and heated at 85° C. for 2.5 h. The mixture was cooled to RT, concentrated, the residue dissolved in MTBE and washed with H2O (2×), then brine (2×), dried (MgSO4), and evaporated to afford ethyl 2-(4-fluoro-2-methyl-5-nitrophenyl)acetate (16.79 g, 81% yield) as a dark orange oil which was used without further purification. MS (ESI) m/z: 242.0 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to RT
  2. concentrationconcentrated
  3. dissolutionthe residue dissolved in MTBE
  4. washwashed with H2O (2×)
  5. dry with materialbrine (2×), dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-c687109cbb1049e5b06fbb6fcb3af57d
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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