Phenol → 2-Methyl-4-nitro-1-phenoxybenzene

HRID 1592818Notes

Reaction equation

HRID 1592818 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[CH3:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[O:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-

Product 1

HCID 186166912-Methyl-4-nitro-1-phenoxybenzene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

1-Fluoro-2-methyl-4-nitrobenzene (9.75 g), phenol (7.10 g), and of Cs2CO3 (41.0 g) were dissolved in 100 mL of DMF and heated to 120° C. overnight. The reaction mixture was taken up in EtOAc and washed with water and brine, and dried over Na2SO4. The solution was concentrated to provide 2-methyl-4-nitro-1-phenoxybenzene as an oil, which was used in Step B without further purification.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-7eb9b7acd49d43539a56a68d39221b51
Source dataset
uspto-grants-2007_11
Patent number
US07294616B2

Reaction notes

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