Bicarbonate Ion → 2-(2-Bromoethyl)pyridine

HRID 1910779Notes

Reaction equation

HRID 1910779 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8]O.P(Br)(Br)[Br:11].C(=O)(O)[O-]>C(OCC)C>[Br:11][CH2:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

5

Reactant 3

HCID 769Bicarbonate IonHCID 76752-(2-Hydroxyethyl)pyridineHCID 24614Phosphorus tribromide

Product 1

HCID 129138582-(2-Bromoethyl)pyridineYield 173.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an ice-cold solution of 2-pyridin-2-yl-ethanol (1 g, 8.1 mmol) in diethyl ether (20 mL) was added freshly distilled phosphorous tribromide (0.75 g, 2.7 mmol) over 15 min. The reaction mixture was warmed to r.t. and stirred for a further 5 hours. The reaction mixture was poured into an excess of cooled bicarbonate solution and extracted with dichloromethane (×2). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to afford 2-(2-bromo-ethyl)-pyridine (0.87 g, 58%) as a liquid.

Workup

  1. extractionextracted with dichloromethane (×2)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9a5e976d99864c469dd9014c1b2243cb
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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