1,10-Phenanthroline, 2-phenyl- synthesis
- Product Name:1,10-Phenanthroline, 2-phenyl-
- CAS Number:109559-47-9
- Molecular formula:C18H12N2
- Molecular Weight:256.3
Yield:109559-47-9 99%
Reaction Conditions:
Stage #1: 1,10-Phenanthroline;phenyllithium in toluene at 0;Inert atmosphere;
Stage #2: with manganese(IV) oxide in dichloromethane;
Steps:
Synthesis of 2-subsituted-1,10-phenanthrolines from 1,10-phenanthroline.
A solution of 1,10-phenanthroline (1 g) in dry, degassed toluene (200 ml) was cooled to 0 °C under argon and subjected to vigorous stirring. The pre-titrated n-butyl- or phenyllithium solution was added dropwise via syringe in the following way: on addition of the first few drops of alkylating reagent, no permanent color change was observed. On further careful addition (typically one drop) the solution became intensely colored, indicating formation of the addition product. From this point 1.0 equiv of lithium reagent was added slowly and the solution left to stir for 5 min. Quenching with H2O (30 ml), extraction with CH2Cl2 (3 × 100 ml) and reoxidation by MnO2 gave the title product. Work-up by filtration of the CH2Cl2 solution through a short plug of alumina and additional washing with CH2Cl2 (2 × 100 ml) gave, after removal of the solvent, the 2-substututed-1,10-phenanthroline in good yields (2-phenyl-1,10-phenanthroline: 99% and 2-butyl-1,10-phenanthroline: 98%, as white powders).
References:
Jakobsen, S?ren;Tilset, Mats [Tetrahedron Letters,2011,vol. 52,# 24,p. 3072 - 3074] Location in patent:experimental part
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