Réaction #430087

Équation de réaction

2-bromo-3,4-bis(decyloxy)-5-(benzothiazol-2-yl)-thiophene

sodium

potassium hydroxide

→

desired product

Rendement 66.5%

3,4,3',4'-tetradecyloxy-5,5'-bis(benzothiazol-2-yl)-2,2'-bithiophene

Rendement 66.5%

Solvants

dioxane

Conditions de réaction

Traitement

1. 1
   Autrewas degassed
2. 2
   Autreby bubbling nitrogen through the solution for 20 min
3. 3
   workup.ADDITIONUnder nitrogen, tetrakistriphenylphosphinopalladium (0.468 g) was added
4. 4
   TempératureAfter cooling
5. 5
   workup.ADDITIONpyridine (5 ml) was added
6. 6
   FiltrationThe separated solids were filtered
7. 7
   workup.ADDITIONthe filtrate diluted with an equal volume of water
8. 8
   ExtractionThe mixture was extracted with an equal volume of toluene
9. 9
   Séchagedried over magnesium sulfate
10. 10
    Concentrationconcentrated
11. 11
    Autrechromatographed over 250 g of silica gel
12. 12
    LavageElution with 3:1 and 2:1 heptane

Mode opératoire

A solution of 2-bromo-3,4-bis(decyloxy)-5-(benzothiazol-2-yl)-thiophene (12.2 g 20 mmol), and hexabutyl ditin (5.8 g, 10 mmol) in dioxane (100 ml), (freshly distilled from sodium after treatment with potassium hydroxide), was degassed by bubbling nitrogen through the solution for 20 min. Under nitrogen, tetrakistriphenylphosphinopalladium (0.468 g) was added and the mixture was heated at 100° C. for 20 hr. After cooling, pyridine (5 ml) was added and the resulting mixture allowed to stand for 1 hr. The separated solids were filtered and the filtrate diluted with an equal volume of water. The mixture was extracted with an equal volume of toluene, dried over magnesium sulfate and concentrated. The residue was combined with the initial solids and chromatographed over 250 g of silica gel. Elution with 3:1 and 2:1 heptane:toluene gave the desired product which was recrystallized from heptane to give 7.02 g (66.5% yield) mp 93.9°-95° C. Mass Spec. m/z 916 (M+ --C10H20). Elemental Analysis: Calculated for C62H92N2O4S4 : C, 70.36, H, 8.77, N, 2.65, and S, 12.10%. Found: C, 69.98, H, 8.90, N, 2.59, and S, 11.98 %.

Source