Dimethylformamide → HCID 67010061, compound

HRID 1630075Notes

Reaction equation

HRID 1630075 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[F:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=2)[NH2:7])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 67010061HCID 67010061, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-chloro-2-nitroaniline (345 mg, 2.00 mmol), 4-fluorophenol (224 mg, 2 mmol), potassium carbonate (549 mg, 4 mmol) and DMF (8 mL) was stirred at 120° C. for 1 day. The mixture was cooled and then water (10 mL) was added. The mixture was extracted with ethyl acetate (4×2 mL). The combined extract was dried over magnesium sulfate and concentrated. Product was purified from the residue by silica gel column chromatography (eluted with a 6:1 mixture of hexane/EtOAc) to give 5-(4-fluorophenoxy)-2-nitroaniline (510 mg, quant) as a yellow powder.

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe mixture was extracted with ethyl acetate (4×2 mL)
  3. extractionThe combined extract
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated
  6. customProduct was purified from the residue by silica gel column chromatography (
  7. washeluted with a 6:1 mixture of hexane/EtOAc)

Sources & evidence

ORD record
ord-2d9c8a3c54a34820bc2bc97fc239d86b
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…