Реакция #2005

Уравнение реакции

water

2-propanol

4-tolylboronic acid

2-bromo-1-nitrobenzene

→

product

Выход 77.4%

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

Выход 77.4%

Растворители

sodium hydroxide

benzene

Условия реакции

Обработка

1. 1
   ТемператураThe two-phase mixture was heated
2. 2
   Температураat reflux for three hours
3. 3
   ДругоеThe cooled reaction mixture
4. 4
   Фильтрацияwas filtered through Celite
5. 5
   Промывкаthe filter cake washed with fresh benzene
6. 6
   ДругоеThe organic layer was separated
7. 7
   Промывкаwashed with water (3×)
8. 8
   Сушкаdried over magnesium sulfate
9. 9
   Фильтрацияfiltered
10. 10
    ДругоеThe filtrate was evaporated under vacuum
11. 11
    Другоеthe residue (46.1 g) purified by preparative high pressure liquid chromatography on silica gel
12. 12
    Промывкаeluting with hexane/ethyl acetate (20:1)

Методика

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.

Источник