Butyl iodide → HCID 18543542, compound

HRID 1533192Notes

Reaction equation

HRID 1533192 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[S-2:12].[Na+].[Na+].I[CH2:16][CH2:17][CH2:18][CH3:19]>CN(C)C=O>[CH2:16]([S:12][C:7]1[CH:6]=[CH:5][C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]=1[Cl:1])[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 14804Sodium SulfideHCID 676882-Chloro-1-fluoro-4-nitrobenzene

Product 1

HCID 18543542HCID 18543542, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-chloro-4-fluoro-nitrobenzene (5.0 g) and sodium sulfide (2.5 g) in N,N-dimethylformamide (30 mL) is stirred at room temperature for 1 hour and then treated with 1-iodobutane (12.6 g). The solvent is then removed under reduced pressure and the resulting residue is treated with ethyl acetate and hexanes to precipitate the inorganic salts. The solids are removed by filtration and the filtrate is reduced under reduced pressure. The resulting residue is then passed through hydrous magnesium silicate using dichloromethane as the eluent to provide the desired compound as a yellow solid.

Workup

  1. customThe solvent is then removed under reduced pressure
  2. additionthe resulting residue is treated with ethyl acetate and hexanes
  3. customto precipitate the inorganic salts
  4. customThe solids are removed by filtration

Sources & evidence

ORD record
ord-443378523e9441b9960c0ff0044a46f1
Source dataset
uspto-grants-2001_03
Patent number
US06207715B1

Reaction notes

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