Water → 4-Chloro-2-fluoro-1-(2,2,2-trifluoroethoxy)benzene

HRID 1964994Notes

Reaction equation

HRID 1964994 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.[F-].[K+].[F:12][C:13]([F:17])([F:16])[CH2:14]I.O>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:14][C:13]([F:17])([F:16])[F:12])=[C:4]([F:9])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 1819754-Chloro-2-fluorophenolHCID 522689Potassium Fluoride

Product 1

HCID 595067484-Chloro-2-fluoro-1-(2,2,2-trifluoroethoxy)benzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To 4-Chloro-2-fluoro-phenol (521, 5.0 g, 0.034 mol) in methanol (50.0 mL) was added potassium fluoride (2.2 g, 0.038 mol). The solvent was removed. The resulting salt was added to N,N-dimethylformaldehyde (25 mL), followed by adding 1,1,1-trifluoro-2-iodo-ethane (8.60 g, 40.9 mmol). The reaction was stirred at 50° C. overnight. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give colorless oil (522, 2.0 g, 26%).

Workup

  1. customThe solvent was removed
  2. additionThe resulting salt was added to N,N-dimethylformaldehyde (25 mL)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with 20% ethyl acetate in hexane
  9. customto give colorless oil (522, 2.0 g, 26%)

Sources & evidence

ORD record
ord-8be34aca1a06423c9d4173a10296fd4a
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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