1-Bromo-2-iodobenzene → 4-(4-Bromophenyl)pyridine

HRID 619819Notes

Reaction equation

HRID 619819 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C([O-])(O)=O.[Na+].C([Li])CCC.I[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Br:26]>>[N:6]1[CH:7]=[CH:8][C:3]([C:24]2[CH:23]=[CH:22][C:21]([Br:26])=[CH:20][CH:25]=2)=[CH:4][CH:5]=1

Participants

5

Reactant 4

HCID 114151-Bromo-2-iodobenzeneHCID 881004-Bromopyridinium chlorideHCID 516892Sodium BicarbonateHCID 178418339Butyllithium

Product 1

HCID 6162834-(4-Bromophenyl)pyridine

Procedure

4-Bromopyridine hydrochloride is free based with saturated NaHCO3 solution and extracted into methylene chloride. The organic solution is concentrated at room temperature and used immediately without further purification. A portion of the solid obtained (3 g, 19 mmol) is treated as described in EXAMPLE 53, Part A with n-butyl lithium (14.25 mL of a 1.6 M solution in TIF, 22.8 mmol) and iodobromobenzene (5.39 g, 19 mmol). The crude product is purified by chromatography (30% EtOAc/hexanes to 60% EtOAc/hexanes) to obtain the title compound (2.59 g, 11.06 mmol).

Workup

  1. extractionextracted into methylene chloride
  2. concentrationThe organic solution is concentrated at room temperature
  3. customused immediately without further purification
  4. customA portion of the solid obtained (3 g, 19 mmol)
  5. additionis treated
  6. customThe crude product is purified by chromatography (30% EtOAc/hexanes to 60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-3d6b7f616b684185882b4b83c12e21f4
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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