Toluene → 5-Bromo-2,3'-bipyridine

HRID 2425800Notes

Reaction equation

HRID 2425800 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][N:12]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[Br:17][C:14]1[CH:15]=[CH:16][C:11]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[N:12][CH:13]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 693532,5-DibromopyridineHCID 27343783-Pyridinylboronic acid

Product 1

HCID 113906775-Bromo-2,3'-bipyridineYield 70.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Into a 1 l flask, 20 g of 3-pyridine boronic acid, 50 g of 2,5-dibromopyridine, 5.5 g of Pd(PPh3)4, 33.9 g of sodium carbonate, 500 ml of toluene, 150 ml of ethanol, and 150 ml of pure water were put, and the solution was stirred at reflux temperature for 3.5 hours. After heating, the reaction liquid was cooled to room temperature and the organic layer was extracted. The organic layer was concentrated in an evaporator, the concentrates were purified by column chromatography, then, recrystallized in heptane, and thus 27 g of 5-bromo-2,3′-bipyridine was obtained.

Workup

  1. temperatureat reflux temperature for 3.5 hours
  2. temperatureAfter heating
  3. customthe reaction liquid
  4. extractionthe organic layer was extracted
  5. concentrationThe organic layer was concentrated in an evaporator
  6. customthe concentrates were purified by column chromatography
  7. customrecrystallized in heptane

Sources & evidence

ORD record
ord-ee080108e90d41d4a6513a5bb5de9243
Source dataset
uspto-grants-2011_06
Patent number
US07964293B2

Reaction notes

Loading…