ChemicalBook CAS DataBase List 6,6'-DIMETHOXY-2-2'-BIPYRIDINE

6,6'-DIMETHOXY-2-2'-BIPYRIDINE synthesis

8synthesis methods

Product Name:6,6'-DIMETHOXY-2-2'-BIPYRIDINE
CAS Number:39858-88-3
Molecular formula:C12H12N2O2
Molecular Weight:216.24

40473-07-2 Synthesis

40473-07-2
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39858-88-3
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Yield:39858-88-3 99%

Reaction Conditions:

with manganese;zirconocene dichloride;[(2,9-dimethyl-1,10-phenanthroline)dichloro nickel(II)];lithium chloride in 1,2-dimethoxyethane at 20; for 12 h;Inert atmosphere;

Steps:

General procedure: To a suspension of a NiCl₂-complex (0.01 mmol, 0.02 equiv), Zr(cp)₂Cl₂ (Strem, 99%; 7.3 mg, 0.025 mmol, 0.05 equiv), Mn powder (Aldrich, 99.99%; 54.9 mg, 1.0 mmol, 2.0 equiv) and LiCl (Aldrich, anhydrous, ground powder; 42.4 mg, 1.0 mmol, 2.0 equiv) in DME (Aldrich, anhydrous, 99.5%; 1.0 mL) was added an iodide (0.5 mmol) under nitrogen. The mixture was stirred at rt under nitrogen until the reaction completed (TLC). Except for the dipyridyls, the mixture was loaded on silica gel directly, and the flash chromatography on silica gel gave the homo-coupling product. For dipyridyls, the reaction was quenched with aq. NH₄OH (27% w/w, 0.6 mL), stirred for 10 min, extracted with CH₂Cl₂ (10 mL × 3), washed with brine (15 mL), dried over Na₂SO₄, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to give the homocoupling product. For alkenyl halide substrates (Fig. 3 and Table 3), the reaction was done in 0.2 mmol scale (C: 0.5 M) with added toluene (42 μl, 0.4 mmol, 2.0 equiv) as an internal standard. After the reaction was completed, a small portion (50 μL) of the mixture was passed through a small silica pad, and eluted with CDCl₃ (1 mL). The yield was estimated from ¹H NMR (600 MHz, CDCl₃).