Sodium Carbonate → 3-(3-Bromophenyl)pyridine
Reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1>C1(C)C=CC=CC=1.C(O)C.C(Cl)Cl>[Br:14][C:15]1[CH:20]=[C:19]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[CH:18]=[CH:17][CH:16]=1Participants
Procedure
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.
Workup
- customat R.T
- additionwere added
- waitThis heterogeneous reaction mixture was vigorously stirred 20 hrs
- temperatureat 80° under nitrogen, cooled
- washwashed with 2×5 mL of 2M aqueous sodium carbonate solution
- additioncontaining 0.5 mL of conc. ammonia
- customThe organic layer was dried over anhyd
- customSolvent removal
- customfollowed by purification on silica gel
Sources & evidence
- ORD record
- ord-a3eab62d3c9248b5b808b7152d17f935
- Source dataset
- uspto-grants-1992_07
- Patent number
- US05128335
Reaction notes
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