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3-(3,4-difluorophenyl)prop-2-yn-1-ol synthesis
- Product Name:3-(3,4-difluorophenyl)prop-2-yn-1-ol
- CAS Number:893747-16-5
- Molecular formula:C9H6F2O
- Molecular Weight:168.14
Yield:893747-16-5 70%
Reaction Conditions:
with bis-triphenylphosphine-palladium(II) chloride;copper(l) iodide;N-ethyl-N,N-diisopropylamine in toluene at -78 - 70; for 8.5 h;Inert atmosphere;
Steps:
1.a; 2
(a) Add 100 ml of toluene to a 1 L three-neck reaction flask.Replaced three times with N2,Add propargyl alcohol (28 g, 500 mmol) and cool to -78 ° C.Add Pd(PPh3)2Cl2 (5.25g, 15 mmol)a mixture with CuI (4.75 g, 50 mmol),Then add N,N-diisopropylethylamine (DIPEA, 129g, 1.0 mol)And 1,2-difluoro-4-iodobenzene (60 g, 500 mmol),Pay attention to temperature control when adding N,N-diisopropylethylamine and 1,2-difluoro-4-iodobenzene.Approx. 30 minutes;The reaction was heated to 70 ° C and stirred for 8 hours (at this point, the TLC determined that the reaction was almost complete),Cool to room temperature,The insoluble matter is washed by filtration through a diatomaceous earth medium,concentrate,Purification by column chromatography gave 29 g of compound 2 (yield 70%, purity 99.5%).
References:
CN108503508,2018,A Location in patent:Paragraph 0009; 0011; 0014