Propargyl bromide → 1-[(Prop-2-yn-1-yl)oxy]-2-(trifluoromethyl)benzene

HRID 1844698Notes

Reaction equation

HRID 1844698 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[CH:12]#[C:13][CH2:14]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:14]([O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:10])([F:11])[F:1])[C:13]#[CH:12]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 679582-Trifluoromethylphenol

Product 1

HCID 534868461-[(Prop-2-yn-1-yl)oxy]-2-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-(trifluoromethyl)phenol (50.0 g, 0.31 mol) and progargyl bromide (44.0 g, 0.37 mol) in ACN (500 mL) was added K2CO3 (51.0 g, 0.37 mol) and the mixture was stirred overnight at rt, concentrated, diluted with water and extracted with Et2O. The combined organic layers were dried over Na2SO4, filtered, concentrated and purified by CC (PE/EA=40/1) to give compound P33a (59.7 g, 97%) as an oil.

Workup

  1. concentrationconcentrated
  2. additiondiluted with water
  3. extractionextracted with Et2O
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by CC (PE/EA=40/1)
  8. customto give compound P33a (59.7 g, 97%) as an oil

Sources & evidence

ORD record
ord-7153c67ecf21467cbf3c81b45529fe39
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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