4-Iodophenol → 1-(3-Chloropropoxy)-4-iodobenzene

HRID 1669741Notes

Reaction equation

HRID 1669741 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:16]([Cl:19])[CH2:17][CH3:18]>CC(=O)CC>[Cl:19][CH2:16][CH2:17][CH2:18][O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 36872Propane, bromochloro-

Product 1

HCID 158955201-(3-Chloropropoxy)-4-iodobenzene

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
82.5 °C

Procedure

A mixture of 4-iodophenol (250 g), potassium carbonate (313.6 g) and 2-butanone (1500 ml) is stirred for 15-20 min. 1-bromochloropropane (357.71 g) is added over about 10 minutes at 25-30° C. After stirring for a further 10 min, the reaction mass is heated to reflux (about 80-85° C.) for 22-24 h. After cooling to 25-30° C., the mixture is filtered, washing the cake with 2-butanone (750 ml). The filtrate is concentrated under reduced pressure at 50-60° C. Ethyl acetate (3750 ml) is added and stirred for 10-20 min to get a clear solution. This is washed with 2N sodium hydroxide solution (1250 ml), water (2500 ml) and aqueous sodium chloride (2500 ml) and then dried with sodium sulfate. The solvent is concentrated under reduced pressure at 50-60° C. n-heptane (250 ml) is added and stirred for about 20 min at 25-30° C. The solution is then cooled to −5 to −10° C. and stirred for about 30 min. The solid is filtered, washed with chilled n-heptane (125 ml, 0-5° C.) and the solid is allowed to dry.

Workup

  1. stirringAfter stirring for a further 10 min
  2. temperaturethe reaction mass is heated
  3. temperatureAfter cooling to 25-30° C.
  4. filtrationthe mixture is filtered
  5. washwashing the cake with 2-butanone (750 ml)
  6. concentrationThe filtrate is concentrated under reduced pressure at 50-60° C
  7. additionEthyl acetate (3750 ml) is added
  8. stirringstirred for 10-20 min
  9. customto get a clear solution
  10. washThis is washed with 2N sodium hydroxide solution (1250 ml), water (2500 ml) and aqueous sodium chloride (2500 ml)
  11. dry with materialdried with sodium sulfate
  12. concentrationThe solvent is concentrated under reduced pressure at 50-60° C. n-heptane (250 ml)
  13. additionis added
  14. stirringstirred for about 20 min at 25-30° C
  15. temperatureThe solution is then cooled to −5 to −10° C.
  16. stirringstirred for about 30 min
  17. filtrationThe solid is filtered
  18. washwashed with chilled n-heptane (125 ml, 0-5° C.)
  19. customto dry

Sources & evidence

ORD record
ord-11f6f5eb0ea143099e16725bab0f2465
Source dataset
uspto-grants-2011_08
Patent number
US07989629B2

Reaction notes

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