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

HRID 1109985Notes

Reaction equation

HRID 1109985 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19]>CN(C=O)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:12]([N+:18]([O-:20])=[O:19])[CH:13]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 69772,5-DichloronitrobenzeneHCID 24758Sodium hydride

Product 1

HCID 8911814-Chloro-2-nitro-1-phenoxybenzeneYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of phenol (36.6 g, 0.39 mol) in DMF (250 mL) was added sodium hydride (10 g, 0.42 mol) in portions. To the resulting solution was added a solution of 2,5-dichloronitrobenzene (68 g, 0.35 mol) in DMF (500 mL), and the mixture was stirred for 16 hours. The solvent was removed under reduced pressure, and the residue was takene up in EtOAc (400 mL) and extracted with brine (saturated, 400 mL). The product was distilled to yield a yellow liquid (84.2 g, 95%), which had a boiling point of 245°-265° C./1.5 mmHg. This material was employed in Example 9 without further purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with brine (saturated, 400 mL)
  3. distillationThe product was distilled

Sources & evidence

ORD record
ord-cdb695e92f814fcc8430a091be32eb99
Source dataset
uspto-grants-1994_06
Patent number
US05324722

Reaction notes

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