Water → 4-Chloro-5-(2-chloro-2-propenyloxy)2-fluoronitrobenzene

HRID 1681090Notes

Reaction equation

HRID 1681090 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].[Cl:13][C:14]([CH2:16]Cl)=[CH2:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[C:3]([O:12][CH2:16][C:14]([Cl:13])=[CH2:15])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 65652,3-DichloropropeneHCID 11430Potassium CarbonateHCID 158655Phenol, 2-chloro-4-fluoro-5-nitro-

Product 1

HCID 198069634-Chloro-5-(2-chloro-2-propenyloxy)2-fluoronitrobenzeneYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-4-fluoro-5-nitrophenol (20.3 g) and 2,3-dichloropropene (11.7 g) was dissolved in N,N-dimethylformamide (200 ml), and potassium carbonate (14.6 g) was added thereto at room temperature, and the resultant mixture was stirred at 80° C. for 2 hours. After cooling to room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was purified by silica gelchromatography (eluent: hexane/ethyl acetate=4/1) to give 4-chloro-5-(2-chloro-2-propenyloxy)2-fluoronitrobenzene (14.8 g; yield, 53%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gelchromatography (eluent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-0d0f495e0dea4d67a3b2d5b244c006c7
Source dataset
uspto-grants-1992_12
Patent number
US05169431

Reaction notes

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