Phosphorus tribromide → 2-Bromo-5-(2-bromoethyl)pyridine

HRID 1400904Notes

Reaction equation

HRID 1400904 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[CH:4][CH:3]=1.P(Br)(Br)[Br:12]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][Br:12])=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 224732202-(6-Bromopyridin-3-yl)ethanol

Product 1

HCID 584744292-Bromo-5-(2-bromoethyl)pyridineYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alcohol 289 (1.75 g, 8.66 mmol) was treated with phosphorous tribromide (5.0 mL, 53 mmol) and the mixture was heated for 5 min, until the solid had melted and re-solidified. The mixture was cooled, treated with ice and partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The organic phase was collected, washed with saturated aqueous sodium bicarbonate and brine, dried (anhydrous MgSO4), filtered and concentrated. Silica gel chromatography of the residue (eluent DCM) provided title compound 290 (2.0 g, 7.6 mmol, 87% yield) as a colorless solid. MS (M+H): 266.0

Workup

  1. temperaturethe mixture was heated for 5 min, until the solid
  2. temperatureThe mixture was cooled
  3. additiontreated with ice
  4. custompartitioned between saturated aqueous sodium bicarbonate and dichloromethane
  5. customThe organic phase was collected
  6. washwashed with saturated aqueous sodium bicarbonate and brine
  7. dry with materialdried (anhydrous MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-13241e01ffea42919998fe0650decba0
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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