3-Chlorophenol → HCID 66602053, compound

HRID 1615459Notes

Reaction equation

HRID 1615459 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.F[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[O:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>O.[Cl-].[Na+].O.C(OCC)(=O)C.C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[O:19][CH3:20]

Participants

9

Reactant 4

HCID 79333-ChlorophenolHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide2×HCID 144519681-Fluoro-2-methoxy-4-nitrobenzene

Product 1

HCID 66602053HCID 66602053, compoundYield 91.8%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
95 °C

Procedure

In a 250 mL round-bottom flask was added 3-chlorophenol (4.13 g, 32.1 mmol), 1-fluoro-2-methoxy-4-nitrobenzene (5.00 g, 29.2 mmol), potassium carbonate (6.06 g, 43.8 mmol) and acetonitrile (25 mL). The reaction was heated to 95° C. for 48 hours. The reaction was cooled to room temperature and was purified by column chromatography on silica gel (hexane/ethyl acetate=3:1). The reaction was poured into sodium hydroxide (2 mol) and extracted with ethyl acetate. The ethyl acetate layers were washed with sodium hydroxide (2 mol), water and brine. The combined organic layers were dried over sodium sulfate, filtered and solvent removed. A small amount of methanol added and oil was triturated to obtain the title compound (7.5 g) having the following physical data.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customwas purified by column chromatography on silica gel (hexane/ethyl acetate=3:1)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customsolvent removed
  7. additionA small amount of methanol added
  8. customoil was triturated

Sources & evidence

ORD record
ord-c6bc0fd3639743f39db62c88afe8b332
Source dataset
uspto-grants-2014_07
Patent number
US08765754B2

Reaction notes

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