反応 #1483118

反応方程式

2-Chloro-1,10-phenanthroline

Na2CO3

ethanol

2-methoxyphenylboronic acid

→

2-(2-Methoxyphenyl)-1,10-Phenanthroline Hydrochloride Chloride

溶媒

toluene

ethyl acetate

反応条件

後処理

1. 1
   温度At the end of this period the reaction was cooled
2. 2
   洗浄The organic layer was washed with water (3×100 mL) and intermittently with brine
3. 3
   その他formed
4. 4
   ろ過The organic layer was filtered through a pad of celite
5. 5
   乾燥dried over MgSO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated to an oil
8. 8
   workup.DISSOLUTIONThe oil was dissolved in CH2Cl2 (20 mL)
9. 9
   workup.ADDITIONdiethyl ether (150 mL) added
10. 10
    workup.ADDITIONWith good stirring, a 20% solution of concentrated HCl in ethanol (20 mL) was added
11. 11
    ろ過The yellow 2-(2-methoxyphenyl)-1,10-phenanthroline hydrochloride chloride was filtered off
12. 12
    洗浄washed with ether
13. 13
    その他air-dried

実験手順

2-Chloro-1,10-phenanthroline (5.9 g, 27.5 mMole), 2-methoxyphenylboronic acid (2) (5 g, 33 mMole), tetrakis(triphenylphosphine)palladium(0) (1 g, 0.825 mMole), 2M-Na2CO3 (33 mL, 66 mMole) and ethanol (8 mL) were suspended in toluene (70 mL) and heated to 100° C. with good stirring for 24 hours. At the end of this period the reaction was cooled, diluted with ethyl acetate (200 mL) and the aqueous layer run off. The organic layer was washed with water (3×100 mL) and intermittently with brine to break up any emulsion formed. The organic layer was filtered through a pad of celite, dried over MgSO4, filtered and concentrated to an oil. The oil was dissolved in CH2Cl2 (20 mL) and diethyl ether (150 mL) added. With good stirring, a 20% solution of concentrated HCl in ethanol (20 mL) was added. The yellow 2-(2-methoxyphenyl)-1,10-phenanthroline hydrochloride chloride was filtered off, washed with ether and air-dried. Yield 9.7 g.

出典