ChemicalBook CAS DataBase List Phenol, 4-(1-propynyl)- (9CI)

Phenol, 4-(1-propynyl)- (9CI) synthesis

5synthesis methods

Product Name:Phenol, 4-(1-propynyl)- (9CI)
CAS Number:170651-15-7
Molecular formula:C9H8O
Molecular Weight:132.16

540-38-5 Synthesis

540-38-5
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74-99-7
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170651-15-7
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Yield:170651-15-7 87%

Reaction Conditions:

Stage #1: p-Iodophenolwith bis-triphenylphosphine-palladium(II) chloride;copper(l) iodide;triethylamine in tetrahydrofuran at 0; for 0.166667 h;Inert atmosphere;Sonication;
Stage #2: prop-1-yne in tetrahydrofuran at -78 - 20;Inert atmosphere;Sonogashira Cross-Coupling;

Steps:

Sonogashira Coupling of Aryl Iodides with Propyne; General Procedure

General procedure: A flame dried flask was charged with THF (1.5 mL/mmol ArI), followed by CuI (10% equiv) and PdCl₂(PPh₃)₂ (2.5% equiv) while argon was bubbled through. The solution was sonicated at 0 °C for the duration of all reagent additions except for propyne. The respective aryl iodide* (1 equiv) was dissolved in THF (1.5 mL/mmol ArI) and added dropwise to the solution, followed by dropwise addition of Et₃N in THF (2-3 equiv/1.5 mL). Addition of reagents during sonication was done over the course of approximately 10 min. The solution was cooled to -78 °C and propyne in THF (2 equiv) was added. The solution was stirred and allowed to reach rt slowly overnight. The reactionwas worked up with sat. aq NH₄Cl (1 × 7 mL/mmol ArI) and brine (3 × 5 mL). The organic fraction was poured directly from the separatory funnel onto a Celite pad topped with Na₂SO₄ and vacuum filtered. EtOAc was poured through to recover the remaining product. The solvent was removed in vacuo, affording a crude dark product with no aryl iodide present by TLC and ¹H NMR analyses. The material was purified by either column chromatography or by vacuum distillation. The column was prepared by a hexane slurry of silica gel and loaded with crude material dissolved in a minimal amount of EtOAc. A gradient from 100% to 80% hexane with 20% EtOAc was performed, yielding the desired product. * Experimental scales from 1 mmol to 6 mmol of the aryl iodide were performed.

References:

Alterman, Joshua L.;Kraus, George A. [Synthesis,2021,vol. 54,# 3,art. no. SS-2021-M0500-PSP,p. 655 - 657]

2749-94-2 Synthesis