Propargyl alcohol → 3-(4-(Trifluoromethyl)phenyl)prop-2-yn-1-ol

HRID 856022Notes

Reaction equation

HRID 856022 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[CH2:12]([OH:15])[C:13]#[CH:14].C(N(CC)CC)C>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([C:14]#[C:13][CH2:12][OH:15])=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-

Product 1

HCID 118304283-(4-(Trifluoromethyl)phenyl)prop-2-yn-1-olYield 60%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromobenzotrifluoride (6.5 g, 28.89 mmol), propargyl alcohol (2.35 ml, 40.45 mmol), triethylamine (5.64 ml, 40.45 mmol), triphenylphosphine (230 mg, 0.87 mmol), cuprous iodide (110 mg, 0.58 mmol), and dichlorobis(triphenylphosphine)palladium (210 mg, 0.29 mmol) in toluene (100 ml) was stirred at 100° C. under a nitrogen atmosphere for 2 hours. The reaction mixture was allowed to return to room temperature and filtered through Celite. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate =9/1) to afford 3-(4-trifluoromethylphenyl)-2-propyn-1-ol (3.47 g, yield 60%) as a pale brown oil.

Workup

  1. customto return to room temperature
  2. filtrationfiltered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate =9/1)

Sources & evidence

ORD record
ord-cff10d4ac69946d5b443283de71be482
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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