Reaktion #2005

Reaktionsgleichung

water

2-propanol

4-tolylboronic acid

2-bromo-1-nitrobenzene

→

product

Ausbeute 77.4%

4-Methyl-2'-nitro-1,1'-biphenyl

Ausbeute 77.4%

Lösungsmittel

sodium hydroxide

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe two-phase mixture was heated
2. 2
   Temperaturat reflux for three hours
3. 3
   SonstigeThe cooled reaction mixture
4. 4
   Filtrationwas filtered through Celite
5. 5
   Waschenthe filter cake washed with fresh benzene
6. 6
   SonstigeThe organic layer was separated
7. 7
   Waschenwashed with water (3×)
8. 8
   Trocknendried over magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    SonstigeThe filtrate was evaporated under vacuum
11. 11
    Sonstigethe residue (46.1 g) purified by preparative high pressure liquid chromatography on silica gel
12. 12
    Wascheneluting with hexane/ethyl acetate (20:1)

Vorschrift

A vigorously stirred mixture of 34 g (0.25 mol) of 4-tolylboronic acid and 34 g (0.17 mol) of 2-bromo-1-nitrobenzene in a mixture of 170 mL of 5N sodium hydroxide, 57 mL of water, 215 mL of 2-propanol and 1080 mL of benzene was treated with 11.9 g of (tetrakis)triphenylphosphine palladium(0). The two-phase mixture was heated at reflux for three hours. The cooled reaction mixture was filtered through Celite and the filter cake washed with fresh benzene. The organic layer was separated and washed with water (3×), dried over magnesium sulfate and filtered. The filtrate was evaporated under vacuum and the residue (46.1 g) purified by preparative high pressure liquid chromatography on silica gel, eluting with hexane/ethyl acetate (20:1), to give 28.05 g of the product.

Quelle