Potassium Iodide → 1-(3-Chloro-propoxy)-2-nitro-benzene

HRID 1162989Notes

Reaction equation

HRID 1162989 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].Br[CH2:12][CH2:13][CH2:14][Cl:15].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[Cl:15][CH2:14][CH2:13][CH2:12][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 69472-NitrophenolHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 114244631-(3-Chloro-propoxy)-2-nitro-benzene

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

2-Nitrophenol (70 mmol), 1-bromo-3-chloropropane (360 mmol), potassium carbonate (water free, 110 mmol), potassium iodide (2 mmol) and tetrabutyl-ammonium bromide (1 mmol) are suspended in acetone (130 ml) and heated up to 50° C. and the mixture is then stirred at this temperature for 30 hours. After cooling down to RT the solid material is filtered off and the filtrate is evaporated. The excess of 1-bromo-3-chloropropane is distilled of under vacuum (70° C.). A yellow-orange oil with Rf=0.55 (hexane/ethyl acetate=2:1) is obtained, which is used in the next step without further purification.

Workup

  1. temperatureAfter cooling down to RT the solid material
  2. filtrationis filtered off
  3. customthe filtrate is evaporated
  4. distillationThe excess of 1-bromo-3-chloropropane is distilled of under vacuum (70° C.)
  5. customA yellow-orange oil with Rf=0.55 (hexane/ethyl acetate=2:1) is obtained
  6. customwhich is used in the next step without further purification

Sources & evidence

ORD record
ord-7e457a0b69bd49889114149e9312754f
Source dataset
uspto-grants-2010_10
Patent number
US07820818B2

Reaction notes

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