Isopropyl iodide → 4-Fluoro-2-isopropoxy-1-nitrobenzene

HRID 518812Notes

Reaction equation

HRID 518812 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:19]([CH3:21])[CH3:20]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH:19]([CH3:21])[CH3:20])[CH:7]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 99375-Fluoro-2-nitrophenolHCID 10796Cesium carbonate

Product 1

HCID 106318324-Fluoro-2-isopropoxy-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 18.0 g of 5-fluoro-2-nitrophenol, 29.0 g of caesium carbonate and 13.7 ml of 2-iodopropane in 119 ml of DMF is stirred at ambient temperature overnight. The mixture is concentrated under vacuum and the residue is taken up with 250 ml of water and extracted twice with 250 ml of ethyl acetate. The organic phases are washed twice with 200 ml of a saturated sodium chloride solution, dried over magnesium sulfate and concentrated under vacuum, so as to obtain 17 g of crude product. The crude product is purified on 400 g of silica, elution being carried out with cyclohexane/ethyl acetate (95/5), so as to obtain 13.0 g of 4-fluoro-1-nitro-2-(propan-2-yloxy)benzene in the form of a light yellow oil.

Workup

  1. concentrationThe mixture is concentrated under vacuum
  2. extractionextracted twice with 250 ml of ethyl acetate
  3. washThe organic phases are washed twice with 200 ml of a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customso as to obtain 17 g of crude product
  7. customThe crude product is purified on 400 g of silica, elution

Sources & evidence

ORD record
ord-f16f2dd567044c47bcb1f2b9f5f1cc1e
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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