Chloroform → HCID 17989402, Verbindung

3-Nitrobiphenyl (3.0 g, 15 mmol), was dissolved in DMF (7.5 ml) and dry chloroform (16.5 mmol). This mixture was added dropwise to a stirred precooled mixture of potassium tert-butoxide (7.2 mg, 60 mmol) in DMF (20 ml) and THF (25 ml), at such a rate that the temperature was maintained between −69 and −73° C. When the addition was complete, the mixture was stirred for a further 1 minute then treated with acetic acid (1.5 ml) in methanol (5 ml) and allowed to warm to room temperature. The mixture was treated with saturated aqueous sodium bicarbonate (50 ml) and extracted with dichloromethane (3×5 ml), the combined organic phase dried (MgSO4), filtered and evaporated, then the residue purified by flash chromatography (ether-hexane). This gave a yellow material which consisted of between 30 and 50% of dichloromethylsubstituted 3-nitrobiphenyl and starting material. The mixture was dissolved in acetonitrile (10 ml) and treated with a solution of silver trifluoromethanesulphonate (15 mmol, 3.84 g) in water (5 ml). The mixture was heated to reflux for 16 h in the dark then cooled, the mixture concentrated in vacuo, filtered and the filtrate extracted with ether (3×50 ml). The combined organic phase was evaporated and purified by flash chromatography to give 3-nitrobiphenyl-4-carbaldehyde;

1. temperatureat such a rate that the temperature was maintained between −69 and −73° C
2. additionWhen the addition
3. extractionextracted with dichloromethane (3×5 ml)
4. dry with materialthe combined organic phase dried (MgSO4)
5. filtrationfiltered
6. customevaporated
7. customthe residue purified by flash chromatography (ether-hexane)
8. customThis gave a yellow material which
9. temperatureThe mixture was heated
10. temperatureto reflux for 16 h in the dark
11. temperaturethen cooled
12. concentrationthe mixture concentrated in vacuo
13. filtrationfiltered
14. extractionthe filtrate extracted with ether (3×50 ml)
15. customThe combined organic phase was evaporated
16. custompurified by flash chromatography

ORD-Eintrag

ord-c9d6f7f5354c45b29e406736282e8bfa

Quelldatensatz

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07220777B2