Dimethylformamide → 1-(2-Chloroethoxy)-2-iodo-4-(trifluoromethoxy)benzene

HRID 1267884Notes

Reaction equation

HRID 1267884 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[OH:13].[Cl:14][CH2:15][CH2:16]OS(C1C=CC(C)=CC=1)(=O)=O.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:14][CH2:15][CH2:16][O:13][C:3]1[CH:4]=[CH:5][C:6]([O:8][C:9]([F:11])([F:12])[F:10])=[CH:7][C:2]=1[I:1]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 11430Potassium CarbonateHCID 27694112-Iodo-4-(trifluoromethoxy)phenol

Product 1

HCID 109046421-(2-Chloroethoxy)-2-iodo-4-(trifluoromethoxy)benzeneYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Iodo-4-(trifluoromethoxy)phenol (10 g, 33 mmol), 2-chloroethyl-p-toluenesulfonate (7.9 g, 34 mmol), N,N′-dimethylformamide (50 mL) and potassium carbonate (9.1 g, 66 mmol) were stirred together at 50° C. for 16 hours and then cooled. The suspension was diluted with water (100 mL) and extracted with 60% diethyl ether/hexane (2×100 mL). The extracts were dried (MgSO4) and concentrated to give the title compound as a solid (12.1 g, 33 mmol).

Workup

  1. temperaturecooled
  2. extractionextracted with 60% diethyl ether/hexane (2×100 mL)
  3. dry with materialThe extracts were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fc75b817bed249a0914dd0dbe7c66fc2
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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