3-Nitrophenylboronic Acid → 4-(3-nitrophenyl)pyridine

HRID 322061Notes

Reaction equation

HRID 322061 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.Br[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.C(=O)(O)[O-].[Na+]>O.COCCOC>[N+:1]([C:4]1[CH:5]=[C:6]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 881004-Bromopyridinium chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 4595574-(3-nitrophenyl)pyridineYield 74.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred mixture of 3-nitrophenylboronic acid (2.00 g), 4-bromopyridine hydrochloride (1.56 g), bis(diphenylphosphino)butanepalladium(II) chloride (0.48 g), sodium bicarbonate (2.69 g), water (30 ml) and 1,2 dimethoxyethane (100 ml) is heated under reflux for 3 hours. The cool mixture is added to water (300 nil) and extracted with chloroform (3×150 ml), and the combined organic extracts washed with water and brine, dried (MgSO4), charcoaled and filtered. The solvent is evaporated to give a residue which is purified by flash chromatography (silica, ether) to give 1.19 g of 4-(3nitrophenyl)pyridine, mp 109-110.5° C. (from acetone/hexane).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with chloroform (3×150 ml)
  4. washthe combined organic extracts washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe solvent is evaporated
  8. customto give a residue which
  9. customis purified by flash chromatography (silica, ether)

Sources & evidence

ORD record
ord-a2d7d4d6842e4ad8b3dc29fdb3948cd5
Source dataset
uspto-grants-2001_04
Patent number
US06211220B1

Reaction notes

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