Sodium Carbonate → 2-(4'-Benzoylphenyl)-5-bromopyridine

HRID 1912222Notes

Reaction equation

HRID 1912222 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.C1(C)C=CC=CC=1>[C:9]([C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=2)=[CH:19][CH:18]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 693532,5-DibromopyridineHCID 41972354-Benzoylbenzeneboronic acid

Product 1

HCID 591563002-(4'-Benzoylphenyl)-5-bromopyridineYield 13.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

2,5-dibromopyridine (15.85 g, 66.0 mmol) was weighed into a reaction vessel in an argon stream and prepared into a solution by the addition of toluene (300 mL). 4-benzoylphenylboronic acid (18.86 g, 83.0 mmol), tetrakis(triphenylphosphine)palladium(0) (3.05 g, 2.6 mmol) and a 1.41 M aqueous sodium carbonate solution (100 mL) were added thereto, and the mixture was stirred at 90° C. for 8 hours. From the obtained reaction mixture, the solid was collected by filtration. This solid was washed with cold toluene and cold diethyl ether in this order. This solid was dissolved in a toluene/chloroform mixed solvent (volume ratio: 2/1) and purified by silica gel column chromatography. The eluate was evaporated to dryness, and the obtained residue was dissolved in a chloroform/ethanol mixed solvent (volume ratio: 9/2) and recrystallized several times to obtain 2-(4′-benzoylphenyl)-5-bromopyridine (3.00 g, 8.87 mmol) as a yellow solid.

Workup

  1. customFrom the obtained reaction mixture
  2. filtrationthe solid was collected by filtration
  3. washThis solid was washed with cold toluene and cold diethyl ether in this order
  4. dissolutionThis solid was dissolved in a toluene/chloroform mixed solvent (volume ratio: 2/1)
  5. custompurified by silica gel column chromatography
  6. customThe eluate was evaporated to dryness
  7. dissolutionthe obtained residue was dissolved in a chloroform/ethanol mixed solvent (volume ratio: 9/2)
  8. customrecrystallized several times

Sources & evidence

ORD record
ord-f1199cbf64a74216b82c39c34a79a36c
Source dataset
uspto-grants-2013_12
Patent number
US08608986B2

Reaction notes

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