Iodoethane → 1-Chloro-4-ethoxy-2-nitrobenzene

HRID 31266

Reaction equation

HRID 31266 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH2:11](I)[CH3:12].C(=O)([O-])[O-:15].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:15][CH2:11][CH3:12])=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 69451-Chloro-2-nitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 2407341-Chloro-4-ethoxy-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

4-Chloro-3-nitrobenzene (5.0 g) was dissolved in acetone and ethyl iodide (2.5 ml) and potassium carbonate (4.4 g) were added. The reaction mixture was stirred at 40° C. for 4½ hours. After cooling to room temperature the mixture was filtered and the filtrate was evaporated to dryness. 1H NMR (400 MHz, d6-DMSO) δ: 7.64 (m, 2H), 7.27 (dd, 1H, J 9.0, 3.1 Hz), 4.12 (q, 2H, J 7.0 Hz), 1.34 (t, 3H, 7.0 Hz).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. filtrationwas filtered
  3. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-1df88fa1025d4b02a5456f6a2a92d6d5
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Linked notes

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