Iodoethane → 1-Chloro-2-iodo-4-ethoxybenzene

HRID 1639932Notes

Reaction equation

HRID 1639932 reaction equation
C([O-])([O-])=O.[K+].[K+].I[CH2:8][CH3:9].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=1[I:18]>CN(C=O)C.CCOCC.O>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:8][CH3:9])=[CH:13][C:12]=1[I:18]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 229287294-Chloro-3-iodophenol

Product 1

HCID 588637541-Chloro-2-iodo-4-ethoxybenzeneYield 87.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584184Diethylether waterSolvent

Conditions

Temperature
50 °C

Procedure

Add 2 g (14.5 mmol) of K2CO3 and 1.16 mL (14.5 mmol) of iodoethane to a solution of 2.45 g (9.6 mmol) of 4-chloro-3-iodophenol in 30 mL of DMF. Heat the reaction mixture at 50° C. while stirring for 3 h, then distribute in 200 mL of ether/water 1:1 mixture. Wash the organic phase with 3×50 mL of water then dry over Na2SO4 and concentrate under reduced pressure. We obtain 2.38 g of 1-chloro-2-iodo-4-ethoxybenzene in the form of oil.

Workup

  1. washWash the organic phase with 3×50 mL of water
  2. dry with materialthen dry over Na2SO4
  3. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-7cf83e164dd2443692e52125f4d5e371
Source dataset
uspto-grants-2012_02
Patent number
US08110579B2

Reaction notes

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