Ethanol → HCID 68984776, compound

HRID 1257188Notes

Reaction equation

HRID 1257188 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].S(=O)(=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 49%

Conditions

Temperature
85 °C

Procedure

A solution of 2-(2-bromo-4-fluoro-5-nitrophenyl)acetic acid (5.00 g, 17.98 mmol) in EtOH (100 mL) was treated with concentrated sulfuric acid (0.999 mL, 17.98 mmol) and heated at 85° C. overnight. The mixture was cooled to RT and the EtOH was removed under reduced pressure. The resulting oil was dissolved in MTBE, washed with water (2×) then brine (2×), dried (MgSO4), and concentrated to dryness. The material was purified by silica gel chromatography (EtOAc/Hex) to afford ethyl 2-(2-bromo-4-fluoro-5-nitrophenyl)acetate (2.679 g, 49% yield) as a yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 8.33 (d, 1H), 8.08 (d, 1H), 4.12 (q, 2H), 3.96 (s, 2H), 1.20 (t, 3H); MS (ESI) m/z: 308.0 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to RT
  2. customthe EtOH was removed under reduced pressure
  3. dissolutionThe resulting oil was dissolved in MTBE
  4. washwashed with water (2×)
  5. dry with materialbrine (2×), dried (MgSO4)
  6. concentrationconcentrated to dryness
  7. customThe material was purified by silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-cd5da96cecb848b2b3acd5b3c69a1169
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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