Ethanol → HCID 68984776, compound

HRID 1930305Notes

Reaction equation

HRID 1930305 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][C:13]([OH:15])=[O:14].OS(O)(=O)=O.[CH3:21][CH2:22]O>>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][C:13]([O:15][CH2:21][CH3:22])=[O:14]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 68986110HCID 68986110, compound

Product 1

HCID 68984776HCID 68984776, compoundYield 87%

Conditions

Temperature
85 °C

Procedure

2-(2-bromo-4-fluoro-5-nitrophenyl)acetic acid (6.04 g, 21.7 mmol) and cone. H2SO4 (1.2 mL) were combined in EtOH (100 mL) and stirred with heating at 85° C. After 1.5 h, the completed reaction was cooled to RT and concentrated as completely as possible. The residue was dissolved in MTBE (50 mL) and washed with H2O (2×), and brine (2×), dried (MgSO4), filtered and evaporated to afford a dark orange oil. The crude was purified by silica gel column chromatography to obtain ethyl 2-(2-bromo-4-fluoro-5-nitrophenyl)acetate (5.8 g, 87% yield).

Workup

  1. customthe completed reaction
  2. temperaturewas cooled to RT
  3. concentrationconcentrated as completely as possible
  4. dissolutionThe residue was dissolved in MTBE (50 mL)
  5. washwashed with H2O (2×), and brine (2×)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto afford a dark orange oil
  10. customThe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8f925c411b054b1c912b3b46a3dfe1ef
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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