Ethyl Acetate → Methyl 5-fluoro-2-(2-nitrophenoxy)benzoate

HRID 1946570Notes

Reaction equation

HRID 1946570 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].F[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 2783186Methyl 5-fluoro-2-hydroxybenzoate

Product 1

HCID 59783776Methyl 5-fluoro-2-(2-nitrophenoxy)benzoateYield 84.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 5-fluoro-2-hydroxybenzoate (2.65 g, 15.6 mmo.) and 1-fluoro-2-nitrobenzene (2.02 g, 14.2 mmol) were dissolved in acetonitrile (30 mL) and cesium carbonate (6.10 g, 18.7 mmol) was added. The reaction mixture was stirred at 80° C. for 60 hours. The mixture was cooled down to room temperature and poured into ethyl acetate. This organic mixture was washed with water and brine, dried over sodium sulfate, filtered and evaporated. The crude was purified by flash chromatography with 10-20% ethyl acetate in hexanes and triturated in ethanol to afford the title compound 18 (3.49 g, 84%) as white solid. LRMS (ESI): (calc) 291.05 (found) 292.2 (MS)+.

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. washThis organic mixture was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude was purified by flash chromatography with 10-20% ethyl acetate in hexanes
  7. customtriturated in ethanol

Sources & evidence

ORD record
ord-ce679b1c39b24498a9037fa88234daf4
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

Loading…