Reaction #1483118

Reaction equation

2-Chloro-1,10-phenanthroline

Na2CO3

ethanol

2-methoxyphenylboronic acid

→

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

Solvents

toluene

ethyl acetate

Conditions

Workup

1. 1
   TemperatureAt the end of this period the reaction was cooled
2. 2
   WashThe organic layer was washed with water (3×100 mL) and intermittently with brine
3. 3
   Otherformed
4. 4
   FiltrationThe organic layer was filtered through a pad of celite
5. 5
   Dryingdried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated 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
    FiltrationThe yellow 2-(2-methoxyphenyl)-1,10-phenanthroline hydrochloride chloride was filtered off
12. 12
    Washwashed with ether
13. 13
    Otherair-dried

Procedure

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.

Source