Phenol → HCID 58118771, compound

HRID 2197527Notes

Reaction equation

HRID 2197527 reaction equation
[F:1][C:2]1[C:8](F)=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[NH2:4].[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]1[C:8]([O:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[NH2:4]

Participants

6

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 27370282,3-Difluoro-6-nitroaniline

Product 1

HCID 58118771HCID 58118771, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2,3-difluoro-6-nitroaniline (200 mg, 1.15 mmol) in DMF (10 ml) was added phenol (108 mg, 1.15 mmol) and potassium carbonate (317 mg, 2.30 mmol). The reaction was heated (120° C.) overnight and then cooled to rt. The reaction was diluted with ethyl acetate (200 mL) and then washed with water (2×100 mL) and brine (100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography using 0-50% ethylacetate/hexane to afford the desired product (267 mg, 94%) 1H NMR (300 MHz, DMSO-d6) 7.85 (dd, J=9.8, 2.2 Hz, 1H), 7.34-7.49 (m, 4H), 7.19-7.27 (m, 1H), 7.08-7.16 (m, 2H), 6.21 (dd, J=9.7, 7.8 Hz, 1H); HPLC RT (Method A) 3.48 min.

Workup

  1. temperaturecooled to rt
  2. washwashed with water (2×100 mL) and brine (100 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0799d71af2ea4149b57958a71474a432
Source dataset
uspto-grants-2012_12
Patent number
US08338594B2

Reaction notes

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