Ethanol → 2-(2-Bromopyridin-3-yl)acetonitrile

HRID 1517581Notes

Reaction equation

HRID 1517581 reaction equation
[Br:1][C:2]1[C:7]([CH2:8]Br)=[CH:6][CH:5]=[CH:4][N:3]=1.[C-:10]#[N:11].[Na+].O.C(O)C>ClCCl>[Br:1][C:2]1[C:7]([CH2:8][C:10]#[N:11])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 8929Sodium CyanideHCID 109010782-Bromo-3-(bromomethyl)pyridine

Product 1

HCID 534035092-(2-Bromopyridin-3-yl)acetonitrileYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-bromo-3-bromomethyl-pyridine (840 mg, 3.35 mmol) and sodium cyanide (187.99 mg, 3.68 mmol) is stirred and refluxed for 1 h in a mixture water (10 mL)-ethanol (2 mL). The reaction mixture is diluted with dichloromethane and washed with saturated aqueous solution of sodium bicarbonate. The organic layer is separated, dried over magnesium sulfate and the solvent evaporated in vacuo to give 83% of the title compound that is used without further purification. MS (m/z): 197 (M+1), 199 (M+3).

Workup

  1. washwashed with saturated aqueous solution of sodium bicarbonate
  2. customThe organic layer is separated
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-259963ad65984f20a3e2916a844a5af0
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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