Sodium Carbonate → 3-(4-Bromophenyl)pyridine

HRID 1878046Notes

Reaction equation

HRID 1878046 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.[Br:10][C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=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.O.C(O)C.COCCOC>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:13][CH:12]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 27343783-Pyridinylboronic acid

Product 1

HCID 15152413-(4-Bromophenyl)pyridine

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

In a 100 mL three-necked flask were placed 2.4 g (20 mmol) of 3-pyridineboronic acid, 5.6 g (19 mmol) of para-bromoiodobenzene, and 4.5 g (42 mmol) of sodium carbonate. The atmosphere in the flask was replaced with nitrogen, and to the flask were added 15 mL of water, 25 mL of DME, and 10 mL of ethanol. The mixture was degassed by being stirred under reduced pressure, to which 0.22 g (0.19 mmol) of tetrakis(triphenylphosphine)palladium(0) was added. The mixture was stirred under nitrogen stream at 80° C. for 12 hours. After a predetermined time, water was added to the mixture, and an organic substance was extracted with chloroform from the aqueous layer. The obtained extract was washed with a saturated aqueous sodium chloride solution together with the organic layer and then dried over magnesium sulfate. The mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and the filtrate was condensed to obtain an oily substance. The obtained substance was purified by silica gel column chromatography (hexane:ethyl acetate=3:1); thus, 1.8 g of the target yellow oily substance was obtained with a yield of 38%.

Workup

  1. customIn a 100 mL three-necked flask were placed
  2. customThe mixture was degassed
  3. additionwas added
  4. extractionan organic substance was extracted with chloroform from the aqueous layer
  5. extractionThe obtained extract
  6. washwas washed with a saturated aqueous sodium chloride solution together with the organic layer
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855)
  9. customcondensed
  10. customto obtain an oily substance
  11. customThe obtained substance was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)
  12. customthus, 1.8 g of the target yellow oily substance was obtained with a yield of 38%

Sources & evidence

ORD record
ord-e74df42c4e8f4b6aa64f7ee18a4ff686
Source dataset
uspto-grants-2012_11
Patent number
US08314101B2

Reaction notes

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