Potassium Iodide → 1-[(2-Methylbut-3-yn-2-yl)oxy]-4-(trifluoromethoxy)benzene

HRID 1656010Notes

Reaction equation

HRID 1656010 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH3:13][C:14](Cl)([C:16]#[CH:17])[CH3:15].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CCCCCC.CCOCC>[CH3:13][C:14]([O:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:9][CH:8]=1)([CH3:15])[C:16]#[CH:17]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 70015p-(Trifluoromethoxy)phenolHCID 706791-Butyne, 3-chloro-3-methyl-

Product 1

HCID 150529171-[(2-Methylbut-3-yn-2-yl)oxy]-4-(trifluoromethoxy)benzeneYield 82.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21584099Diethylether hexaneSolvent

Procedure

To a solution of p-trifluoromethoxy phenol (30.69 g), and 2-methyl-2-chloro-3-butyne (53.00 g) in dry acetonitrile (350 mi) was added potassium iodide (14.30 g) followed by potassium carbonate (95.25 g). This reaction mixture was heated at 70°-80° C. for four days then cooled to room temperature and filtered through celite. The precipitate was washed with dichloromethane and the washings were added to the acetonitrile. The organics were evaporated in vacuo and the oil was taken up in 250 mL of dichloromethane. The organics were washed with water (2×100 mL) and dilute aqueous sodium thiosulfate (2×100 mL), dried (MgSO4), filtered and evaporated in vacuo to leave a dark brown-orange oil. Flash column chromatography on SiO2 using hexane/Et2O (5/1) afforded 34.73 g of the pure product.

Workup

  1. temperatureThis reaction mixture was heated at 70°-80° C. for four days
  2. filtrationfiltered through celite
  3. washThe precipitate was washed with dichloromethane
  4. additionthe washings were added to the acetonitrile
  5. customThe organics were evaporated in vacuo
  6. washThe organics were washed with water (2×100 mL) and dilute aqueous sodium thiosulfate (2×100 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto leave a dark brown-orange oil

Sources & evidence

ORD record
ord-6924e650979640d18f2713bdeccd81d1
Source dataset
uspto-grants-1993_10
Patent number
US05252597

Reaction notes

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