2-Bromopyridine → 2-(4-Nitrophenyl)pyridine

HRID 1592811Notes

Reaction equation

HRID 1592811 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[N+:8]([C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1)([O-:10])=[O:9].C(COC)OC.C(=O)([O-])[O-].[K+].[K+]>O>[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 79732-BromopyridineHCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 27735524-Nitrophenylboronic acid

Product 1

HCID 4595562-(4-Nitrophenyl)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

2-Bromopyridine (650 μL), 4-nitrophenylboronic acid (1.479 g) and palladium tetrakistriphenylphosphine (391.5 mg) were added to a mixture of 40 mL of dimethoxyethane and 10 mL of 2.0 M aqueous potassium carbonate under an atmosphere of dry N2. The reaction mixture was heated at 95° C. overnight. The reaction mixture was then cooled to room temperature and diluted with water (200 mL). The resulting precipitate was collected, washed with water and air-dried. The dried material was purified using silica gel chromatography to give 1.40 g of 2-(4-nitrophenyl)pyridine.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customThe resulting precipitate was collected
  3. washwashed with water
  4. customair-dried
  5. customThe dried material was purified

Sources & evidence

ORD record
ord-c6120354f014432089d226e5735df3d9
Source dataset
uspto-grants-2007_11
Patent number
US07294616B2

Reaction notes

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