Hydrogen Bromide → 5-Bromo-2-(bromomethyl)pyridine

HRID 2041306Notes

Reaction equation

HRID 2041306 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][N:4]=1.[BrH:10]>>[Br:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][Br:10])=[N:4][CH:5]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 5200169(5-Bromopyridin-2-yl)methanol

Product 1

HCID 234380625-Bromo-2-(bromomethyl)pyridineYield 87%

Conditions

Temperature
150 °C

Procedure

Dissolve 2-hydroxymethyl-5-bromopyridine (5.21 g, 27.7 mmol) in 48% aqueous hydrobromic acid (20 mL). Heat the mixture at 150° C. for 2 h. Cool to ambient temperature and remove excess hydrobromic acid under vacuum. Dilute with water, add cautiously saturated aqueous NaHCO3 and extract three times with EtOAc. Dry over anhydrous Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1) to give the title compound as pink oil (6.0 g, 87%) that crystallizes in the freezer.

Workup

  1. temperatureCool to ambient temperature
  2. customremove excess hydrobromic acid under vacuum
  3. additionDilute with water
  4. additionadd cautiously saturated aqueous NaHCO3
  5. extractionextract three times with EtOAc
  6. dry with materialDry over anhydrous Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customPurify by chromatography on silica gel eluting with hexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-496196381dac4cb49e48c3a9aff14c88
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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