3-Chlorophenol → 2-Chloro-1-(3-chlorophenoxy)-4-nitrobenzene

HRID 38241

Reaction equation

HRID 38241 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.[Cl:12][C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([Cl:12])[CH:14]=1

Participants

5

Reactant 3

HCID 79333-ChlorophenolHCID 10796Cesium carbonateHCID 676882-Chloro-1-fluoro-4-nitrobenzene

Product 1

HCID 2752072-Chloro-1-(3-chlorophenoxy)-4-nitrobenzeneYield 100%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

According to Scheme 3 Step 1, Method A: 2-Chloro-1-fluoro-4-nitrobenzene (1.12 mmol, 0.20 g) was added to a suspension of 3-chlorophenol (1.02 mmol, 0.10 mL), Cs2CO3 (1.25 mmol, 407 mg) in DMF/ACN (40:60, 3.6 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with water. The aqueous phase was extracted with AcOEt. The organic phase was washed with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude product was used without further purification to obtain 2-chloro-1-(3-chlorophenoxy)-4-nitrobenzene (1.02 mmol, 288 mg, 100%) as an orange solid.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionThe aqueous phase was extracted with AcOEt
  3. washThe organic phase was washed with brine
  4. dry with materialwas dried over MgSO4
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure
  7. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-b52fe3e2f3204a35b4cfbbf66d690716
Source dataset
uspto-grants-2013_09
Patent number
US08524726B2

Linked notes

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