Sodium Iodide → HCID 23081477, compound

HRID 856020Notes

Reaction equation

HRID 856020 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.Br[CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C.O>[F:11][C:8]([F:9])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:13][CH2:14][O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 678744-(Trifluoromethyl)phenolHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyran

Product 1

HCID 23081477HCID 23081477, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-hydroxybenzotrifluoride (2.08 g, 12.83 mmol), 2-(2-bromoethoxy)tetrahydropyran (3 g, 14.11 mmol), potassium carbonate (1.95 g, 14.11 mmol), and sodium iodide (2 g, 13.47 mmol) in DMF (15 ml) was stirred at 100° C. for 3 hours. The reaction mixture was allowed to return to room temperature, poured into water, and extracted with ethyl acetate twice. The extract was washed with water twice and brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to afford 2-[2-(4-trifluoromethylphenoxy)ethoxy]tetrahydropyran (2.47 g, yield 66%) as a colorless oil.

Workup

  1. customto return to room temperature
  2. extractionextracted with ethyl acetate twice
  3. washThe extract was washed with water twice
  4. dry with materialbrine, and dried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-61db3bc13b25401b9eb16204e0373c12
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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