Water → 4-(4-Chloro-2-nitro-phenoxy)-benzonitrile

HRID 2197902Notes

Reaction equation

HRID 2197902 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)#[N:13].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([O:20][C:17]2[CH:18]=[CH:19][C:14]([C:12]#[N:13])=[CH:15][CH:16]=2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 27949042-Bromo-5-chloronitrobenzene

Product 1

HCID 92134304-(4-Chloro-2-nitro-phenoxy)-benzonitrileYield 77.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1-Bromo-4-chloro-2-nitrobenzene (10 g, 42.3 mmol) was added to a solution of 4-cyanophenol (5.0 g, 42.3 mmol), and K2CO3 (14.6 g, 0.10 mol) in DMF (50 mL). The mixture was heated at 80° C. for 15 hr. The reaction was poured into water. The aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with water, brine, and dried over sodium sulfate. The organic phase was filtered and concentrated under vacuum. The residue was purified by flash chromatography eluting with (hexanes/ethyl acetate 4:1) to give the product (9.0 g, 77.8%).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. washthe combined organic phases were washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationThe organic phase was filtered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography
  7. washeluting with (hexanes/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-af86d92e90934872aff2e692a71b5911
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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