Potassium Carbonate → HCID 52466667, compound

HRID 2197927Notes

Reaction equation

HRID 2197927 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[OH:12][C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:19]([O:18][C:16](=[O:17])[C:15]1[CH:21]=[CH:22][CH:23]=[C:13]([O:12][C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH:14]=1)[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24522Ethyl 3-hydroxybenzoateHCID 677672,5-Difluoronitrobenzene

Product 1

HCID 52466667HCID 52466667, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

2,5-Difluoronitrobenzene (5.0 g, 31.4 mmol), ethyl 3-hydroxybenzoate (5.2 g, 31.4 mmol), and K2CO3 (8.7 g, 62.8 mmol) were added to DMF (50 mL). The solution was heated to 85° C. and stirred for 16 h. The reaction was cooled. The reaction was poured into distilled water and extracted with ethyl acetate. The combined organic layers were washed with distilled water, brine, and dried over sodium sulfate, filtered and concentrated under vacuum giving the crude title compound. The crude product was purified by silica gel column chromatography eluting with hexanes/ethyl acetate (90:10) to give the title compound (7.0 g, 73%).

Workup

  1. temperatureThe reaction was cooled
  2. additionThe reaction was poured
  3. distillationinto distilled water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with distilled water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customgiving the crude title compound
  10. customThe crude product was purified by silica gel column chromatography
  11. washeluting with hexanes/ethyl acetate (90:10)

Sources & evidence

ORD record
ord-5a3ec2442ab540fabae178de907d7ea0
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

Loading…