Iodoethane → 1-Ethoxy-2-iodo-4-nitrobenzene

HRID 1593763Notes

Reaction equation

HRID 1593763 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[CH2:12](I)[CH3:13].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[CH2:12]([O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[I:1])[CH3:13]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2849492-iodo-4-nitrophenol

Product 1

HCID 574195081-Ethoxy-2-iodo-4-nitrobenzeneYield 22.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-iodo-4-nitrophenol (21 g, 79.2 mmol) [ref: Kometani, T.; Watt, D. S.; Ji, T., Tetrahedron Lett. (1985), 26(17), 2043], ethyl iodide (9 mL, 0.48 mol) and potassium carbonate (40.7 g, 0.3 mol) in 100 mL of N,N-dimethylformamide was heated at 70° C. for 3 hours. The reaction was cooled to room temperature and ethyl acetate was added. The inorganic salts were filtered and washed with ethyl acetate. The organic material was washed with water (3×) and brine, dried over magnesium sulfate and filtered. Upon concentration of the filtrate a solid appeared. This solid was filtered and washed with hexanes to give 5.2 g of 1-ethoxy-2-iodo-4-nitrobenzene as white crystals. Concentration of the filtrate provided an additional 11.3 g of the desired product, mp 81-83° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.42 (t, 3H), 4.26 (q, 2H), 7.18 (d, 1H), 8.26 (dd, 1H), 8.55 (d, 1H)

Workup

  1. filtrationThe inorganic salts were filtered
  2. washwashed with ethyl acetate
  3. washThe organic material was washed with water (3×) and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. filtrationThis solid was filtered
  7. washwashed with hexanes

Sources & evidence

ORD record
ord-bd62b9e1c8ac4cf0901bfaa84e59c6de
Source dataset
uspto-grants-2007_11
Patent number
US07297795B2

Reaction notes

Loading…