반응 #2005

반응 방정식

water

2-propanol

4-tolylboronic acid

2-bromo-1-nitrobenzene

→

product

수율 77.4%

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

수율 77.4%

용매

sodium hydroxide

benzene

반응 조건

후처리

1. 1
   온도The two-phase mixture was heated
2. 2
   온도at reflux for three hours
3. 3
   기타The cooled reaction mixture
4. 4
   여과was filtered through Celite
5. 5
   세척the filter cake washed with fresh benzene
6. 6
   기타The organic layer was separated
7. 7
   세척washed with water (3×)
8. 8
   건조dried over magnesium sulfate
9. 9
   여과filtered
10. 10
    기타The filtrate was evaporated under vacuum
11. 11
    기타the residue (46.1 g) purified by preparative high pressure liquid chromatography on silica gel
12. 12
    세척eluting with hexane/ethyl acetate (20:1)

실험 절차

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.

출처