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

HRID 448379Notes

Reaction equation

HRID 448379 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.I[CH:13]([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH:13]([CH3:15])[CH3:14])[CH:7]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium Carbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-fluoro-2-nitrophenol (2.5 g, 15.9 mmol), 2-iodopropane (5.4 g, 31.8 mmol), and potassium carbonate (4.2 g, 39.8 mmol) in acetone (40 mL) was heated to reflux for 16 hours. The mixture was cooled and evaporated under vacuum, and the residue was partitioned between ethyl acetate (100 mL) and water (150 mL), and the aqueous phase was extracted with ethyl acetate (100 mL). The combined organic layers were washed with water (3×150 mL), dried (MgSO4), and evaporated, providing 3.2 g, in quantitative yield; 1H NMR (CDCl3) δ 1.42 (d, J=6.0 Hz, 6H), 4.63 (septet, J=6.0 Hz, 6H), 6.64-6.72 (m, 1H), 6.76 (dd, J=9.8 Hz, J=2.5 Hz, 1H), 7.88 (dd, J=8.9 Hz, J=6.1 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. temperatureThe mixture was cooled
  4. customevaporated under vacuum
  5. customthe residue was partitioned between ethyl acetate (100 mL) and water (150 mL)
  6. extractionthe aqueous phase was extracted with ethyl acetate (100 mL)
  7. washThe combined organic layers were washed with water (3×150 mL)
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customproviding 3.2 g

Sources & evidence

ORD record
ord-7b6241e8aca64547b4170d1c0a60b6d5
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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