M-Cresol → HCID 22261975, compound

HRID 1610353Notes

Reaction equation

HRID 1610353 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[F:9][C:10]([F:16])([CH:13]([F:15])[F:14])[CH2:11]I.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[F:9][C:10]([F:16])([CH:13]([F:15])[F:14])[CH2:11][O:1][C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 342M-CresolHCID 11430Potassium CarbonateHCID 5428611,1,2,2-Tetrafluoro-3-iodopropane

Product 1

HCID 22261975HCID 22261975, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-hydroxytoluene (5.0 g, 46.2 mmol) in N,N-dimethylformamide (50 ml) were added 2,2,3,3-tetrafluoro-1-iodopropane (12.3 g, 50.9 mmol) and potassium carbonate (12.8 g, 92.5 mmol) and the mixture was stirred overnight at 80° C. The reaction solution was diluted with water (200 ml) and extracted with diethyl ether (300 ml×2). The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 3-(2,2,3,3-tetrafluoropropyloxy)toluene (10.0 g, 97%) as a colorless oil.

Workup

  1. extractionextracted with diethyl ether (300 ml×2)
  2. washThe extract was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-36f002cc67be4d8eb972c3a18585d6fb
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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