Hydrogen Bromide → 2-(2-Bromoethyl)pyridine

HRID 1770097Notes

Reaction equation

HRID 1770097 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[BrH:10]>>[Br:10][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 76752-(2-Hydroxyethyl)pyridine

Product 1

HCID 129138582-(2-Bromoethyl)pyridineYield 100%

Procedure

To 2-(hydroxyethyl)pyridine (10 mL, 88.8 mmol) was added HBr (conc) (90 mL). The mixture was heated to reflux overnight. The next day, excess HBr was removed and the resulting solid recrystallized from iPrOH to provide 2-(bromoethyl)pyridine, yield=100%. 1H NMR (300 MHz, DMSO) δ3.0 (t, 2H), 3.9 (t, 2H), 7.79 (t, 1H), 7.8 (d, 1H), 8.4 (t, 1H), 8.7 (d, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customThe next day, excess HBr was removed
  4. customthe resulting solid recrystallized from iPrOH

Sources & evidence

ORD record
ord-525ad08a6fd14a878688a5bc45490124
Source dataset
uspto-grants-1995_01
Patent number
US05385908

Reaction notes

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