Propargyl bromide → 1-(Prop-2-ynyloxy)-2-(trifluoromethoxy)benzene

HRID 536450Notes

Reaction equation

HRID 536450 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]#[CH:21]>C(#N)C.O>[CH2:21]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[O:3][C:2]([F:11])([F:12])[F:1])[C:20]#[CH:19]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 27772992-(Trifluoromethoxy)phenol

Product 1

HCID 233934371-(Prop-2-ynyloxy)-2-(trifluoromethoxy)benzeneYield 107.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-trifluoromethoxyphenol (10.0 g, 56.1 mmol) in acetonitrile (120 mL) was added potassium carbonate (9.31 g, 67.4 mmol) and propargyl bromide (80% in toluene, 10.0 g, 7.70 mL, 67.4 mmol). The reaction mixture was stirred at ambient temperature for seven days, then diluted with water (150 mL) and extracted with diethyl ether (300 mL). The organic layer was separated and concentrated to obtain the title compound (13.05 g) which was used without further purification in the next step.

Workup

  1. extractionextracted with diethyl ether (300 mL)
  2. customThe organic layer was separated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e628bdc37ccd441c99c7eee47e218df7
Source dataset
uspto-grants-2014_10
Patent number
US08859584B2

Reaction notes

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