反応 #2005

反応方程式

water

2-propanol

4-tolylboronic acid

2-bromo-1-nitrobenzene

→

product

収率 77.4%

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

収率 77.4%

溶媒

sodium hydroxide

benzene

反応条件

後処理

1. 1
   温度The two-phase mixture was heated
2. 2
   温度at reflux for three hours
3. 3
   その他The cooled reaction mixture
4. 4
   ろ過was filtered through Celite
5. 5
   洗浄the filter cake washed with fresh benzene
6. 6
   その他The organic layer was separated
7. 7
   洗浄washed with water (3×)
8. 8
   乾燥dried over magnesium sulfate
9. 9
   ろ過filtered
10. 10
    その他The filtrate was evaporated under vacuum
11. 11
    その他the residue (46.1 g) purified by preparative high pressure liquid chromatography on silica gel
12. 12
    洗浄eluting with hexane/ethyl acetate (20:1)

実験手順

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.

出典