Sodium Carbonate → 4-(4-Bromophenyl)pyridine

HRID 1636993Notes

Reaction equation

HRID 1636993 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.[Br:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1>C1C=CC=CC=1.C(O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 142684-BromopyridineHCID 79599(4-Bromophenyl)boronic acid

Product 1

HCID 6162834-(4-Bromophenyl)pyridineYield 82.4%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

Aq. 2 M sodium carbonate (3 mL)was added to a suspension of 400 mg (2.0 mmol) of 4-bromopyridine in 2 mL of benzene to give 2 clear phases, and argon was bubbled through the mixture for a few minutes before added 115 mg (0.10 mmol) of palladium tetrakis(triphenylphosphine). To the resulting mixture was added a solution of 200 mg (1.00 mmol) of 4-bromophenylboronic acid in 1 mL of ethanol, and the mixture was heated at reflux for 4 h. After cooling to room temperature, the mixture was partitioned between ethyl acetate (25 mL) and water (25 mL). The organic layer was dried over sodium sulfate and concentrated. Purification of the residue by silica gel chromatography, eluting with 25% to 50% ethyl acetate in hexane, gave 193 mg (82%) of 4-(4-bromophenyl)pyridine as a white solid: mp 124-126° C.

Workup

  1. customto give 2 clear phases, and argon
  2. customwas bubbled through the mixture for a few minutes
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 4 h
  5. customthe mixture was partitioned between ethyl acetate (25 mL) and water (25 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. customPurification of the residue by silica gel chromatography
  9. washeluting with 25% to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-43f0123bc7914220abcc7314f9c56554
Source dataset
uspto-grants-2000_03
Patent number
US06037472

Reaction notes

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