Phenol → HCID 67397106, compound

HRID 471581Notes

Reaction equation

HRID 471581 reaction equation
[N+]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=1[C:6]#[N:7])([O-])=O.[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[N+:12]([C:8]1[CH:9]=[CH:10][CH:11]=[C:4]([O:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]=1[C:6]#[N:7])([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 520718Dinitrobenzonitrile

Product 1

HCID 67397106HCID 67397106, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,6-dinitrobenzonitrile (2.0 g, 10.5 mmol), phenol (1.42 g, 15.1 mmol) and K2CO3 (1.45 g, 10.5 mmol) in DMF (20 mL) was stirred at rt under N2 for 4.5 hours. Upon completion, the reaction was diluted with EtOAc (100 mL), washed with H2O, dried over MgSO4, filtered and concentrated. The residue was recrystallized from Hexane/EtOAc to provide 2-nitro-6-phenoxybenzonitrile (1.94 g, 77%). 1H NMR (400 MHz, MeOD) δ 7.20 (m, 2H), 7.28 (dd, J=8.6, 1.1 Hz, 1H), 7.34 (m, 1H), 7.51 (m, 2H), 7.78 (t, J=8.7 Hz, 1H), 8.05 (dd, J=8.2, 0.8 Hz, 1H).

Workup

  1. washwashed with H2O
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was recrystallized from Hexane/EtOAc

Sources & evidence

ORD record
ord-9af2180cff7a4c659844c43318eb2408
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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