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

HRID 1930409Notes

Reaction equation

HRID 1930409 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, 1.00 eq) and cone. H2SO4 (4.00 ml) were combined in EtOH (300 ml) and stirred with heating at 85° C. After 2.5 h, the completed reaction was cooled to RT and concentrated as completely as possible. The residue was dissolved in MTBE (250 ml) and washed with H2O (2×) and brine (2×), dried (MgSO4), filtered 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 as is in the next reaction. MS (ESI) m/z: 242.0 (M+H)+.

Workup

  1. customthe completed reaction
  2. temperaturewas cooled to RT
  3. concentrationconcentrated as completely as possible
  4. dissolutionThe residue was dissolved in MTBE (250 ml)
  5. washwashed with H2O (2×) and brine (2×)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-560f69e008cd4b729a628cdbad354b63
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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