Cesium carbonate → HCID 21930390, compound

HRID 1243734Notes

Reaction equation

HRID 1243734 reaction equation
F[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[OH:12][C:13]1[C:14]([O:21][CH3:22])=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Na+]>CN(C=O)C>[CH3:22][O:21][C:14]1[C:13]([O:12][C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=[O:17]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 118049533-Hydroxy-2-methoxybenzaldehyde

Product 1

HCID 21930390HCID 21930390, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluoro-4-methyl-1-nitrobenzene (0.25 g, 1.6 mmol), 3-hydroxy-2-methoxybenzaldehyde (0.25 g, 1.6 mmol) and cesium carbonate (0.54 g, 1.6 mmol) were heated with stirring in dry DMF (4 mL) at 50° C. for 20 h. The reaction mixture was cooled, poured into 0.1N sodium hydroxide solution and extracted with diethyl ether. The ether layer was separated, washed with 0.1N sodium hydroxide solution (4×), water (4×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to give 2-methoxy-3-(5-methyl-2-nitrophenoxy)benzaldehyde (0.36 g, 77%) as a brown oil, which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with diethyl ether
  3. customThe ether layer was separated
  4. washwashed with 0.1N sodium hydroxide solution (4×), water (4×), brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c9152e6daf944267b43a570c78156319
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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