Phosphorus tribromide → 3-Bromo-5-(1-bromoethyl)pyridine

HRID 712748Notes

Reaction equation

HRID 712748 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8](O)[CH3:9])[CH:5]=[N:6][CH:7]=1.P(Br)(Br)[Br:12].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH:8]([Br:12])[CH3:9])[CH:3]=1

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 129974353-Bromo-5-(1-hydroxyethyl)pyridine

Product 1

HCID 1025488553-Bromo-5-(1-bromoethyl)pyridineYield 43.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(5-Bromo-pyridin-3-yl)-ethanol (1.5 g, 7.4 mmol) is dissolved in DCM (70 mL) and phosphorus tribromide (0.73 mL, 7.4 mmol) is added. The mixture is stirred for 4 hrs and saturated NaHCO3 aqueous solution is used to adjust the pH to about 7. The mixture is then extracted with DCM (3×50 mL). The organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 850 mg of 3-bromo-5-(1-bromo-ethyl)-pyridine.

Workup

  1. extractionThe mixture is then extracted with DCM (3×50 mL)
  2. concentrationconcentrated
  3. customto give the crude product
  4. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-9383dfed97ab407e94f8081299d2b03b
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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