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

HRID 446855Notes

Reaction equation

HRID 446855 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[OH:25]>CN(C)C=O>[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[O:25][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

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

Product 1

HCID 7759752,4-Dichloro-1-(2-nitrophenoxy)benzeneYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-fluoro-2-nitrobenzene (4.8 mL, 45.42 mmol), potassium carbonate (13.8 g, 0.1 mol) and 2,4-dichloro-phenol (8.16 g, 50.06 mmol) in dry dimethylformamide (70 mL) was stirred at 100° C. for 2 h. Solids were filtered off, and the filtrate was concentrated in vacuo. The residue was partitioned between diethyl ether and 1N sodium hydroxide, the organic layer was washed with 1N sodium hydroxide, water and brine, dried over sodium sulfate, filtered and concentrated in vacuo to yield 11.69 g (91%) of the title compound as a yellowish oil, which solidifies on standing. Mp: 58-59° C. MS (EI) 285.2 (MH+). Lit. [Chem. Heterocycl. Compd. (Engl. Transl.) 11 (1975) 1356-1358] Mp: 57-58° C.

Workup

  1. filtrationSolids were filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was partitioned between diethyl ether and 1N sodium hydroxide
  4. washthe organic layer was washed with 1N sodium hydroxide, water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae6c409f0ee04ca4b2af36975afc1470
Source dataset
uspto-grants-2013_07
Patent number
US08481527B2

Reaction notes

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