反応 #740801

反応方程式

sodium carbonate

3-bromopyridine

3-bromophenylboronic acid

→

3-(3'-bromophenyl)pyridine

収率 35.0%

溶媒

ethanol

methylene chloride

toluene

反応条件

後処理

1. 1
   その他at R.T
2. 2
   workup.ADDITIONwere added
3. 3
   workup.WAITThis heterogeneous reaction mixture was vigorously stirred 20 hrs
4. 4
   温度at 80° under nitrogen, cooled
5. 5
   洗浄washed with 2×5 mL of 2M aqueous sodium carbonate solution
6. 6
   workup.ADDITIONcontaining 0.5 mL of conc. ammonia
7. 7
   その他The organic layer was dried over anhyd
8. 8
   その他Solvent removal
9. 9
   その他followed by purification on silica gel

実験手順

Tetrakis-(triphenylphosphine)palladium (153 mG; 0.135 mM) was added to a stirred solution of 3-bromopyridine (0.434 mL; 4.5 mM) in 9 mL of toluene. The resulting solution was stirred 10 mins. under nitrogen at R.T. 2M aqueous sodium carbonate solution (5 mL; 10 mM) followed by a solution of 3-bromophenylboronic acid (1 G; 5 mM) in 2.5 mL of absolute ethanol were added. This heterogeneous reaction mixture was vigorously stirred 20 hrs. at 80° under nitrogen, cooled, diluted with 25 mL of methylene chloride, and washed with 2×5 mL of 2M aqueous sodium carbonate solution containing 0.5 mL of conc. ammonia. The organic layer was dried over anhyd. magnesium sulfate. Solvent removal followed by purification on silica gel using ether:petroleum ether (1:1) as solvent gave 3-(3'-bromophenyl)pyridine in 35% yield as a colorless liquid boiling at 140°-2°/~2 mm.

出典