2,4-Dichlorophenol → 2,4-Dichloro-1-(2-nitrophenoxy)benzene

HRID 1642224Notes

Reaction equation

HRID 1642224 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 84492,4-DichlorophenolHCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 7759752,4-Dichloro-1-(2-nitrophenoxy)benzeneYield 97.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Previously described: Burnistov, S. I.; Karpishchenko, L. S. Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya 1976, 19(1), 39-41. Commercially available Literature mp: 57-58° C. 69-69.6° C. AMR01025 A mixture of 2,4-dichlorophenol (2.00 g, 12.27 mmol), 1-fluoro-2-nitrobenzene (2.07 g, 14.72 mmol) and potassium carbonate (2.04 g, 14.72 mmol) in dimethylformamide (DMF, 10 mL) was stirred under reflux for 1.5 h. After removal of DMF, the residue was dissolved in DCM and washed with NaOH (5%, 3×20 mL) and brine. The organic layer was dried (MgSO4), filtered and evaporated. Flash chromatography on silica gel of the crude product using DCM as eluent gave 1-(2,4-dichlorophenoxy)-2-nitrobenzene (3.4 g, 97%) as a cream oil. Rf: 0.73 (DCM) 1H NMR (270 MHz, CDCl3) δ 6.85 (1H, dd, J=8.4, 1.2 Hz), 6.97 (1H, d, J=8.9 Hz), 7.23 (2H, m), 7.48 (1H, d, J=2.5 Hz), 7.51 (1H, m) and 7.98 (1H, dd, J=8.2, 1.7 Hz). AMR01043 Following the same procedure, from 2,4-dichlorophenol (3.00 g, 18.40 mmol), 1-fluoro-2-nitrobenzene (2.60 g, 18.40 mmol) and potassium carbonate (2.54 g, 18.40 mmol) in dimethylformamide (DMF, 15 mL), and after a reaction time of 3 h, gave AMR01043 (4.89 g, 93%) as a cream solid, mp: 51-54° C.

Workup

  1. custom69-69.6° C
  2. temperatureunder reflux for 1.5 h
  3. customAfter removal of DMF
  4. dissolutionthe residue was dissolved in DCM
  5. washwashed with NaOH (5%, 3×20 mL) and brine
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-0b660d887a8b4f30b49e18c622495a0d
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

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