Dichloromethane → 5-Bromo-6-methoxy-3-pyridineacetonitrile

HRID 554653Notes

Reaction equation

HRID 554653 reaction equation
[Br:1][C:2]1[C:3]([O:10][CH3:11])=[N:4][CH:5]=[C:6]([CH2:8]Br)[CH:7]=1.[C-:12]#[N:13].[Na+].C(Cl)Cl.C([O-])(O)=O.[Na+]>CCO.O>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:12]#[N:13])[CH:5]=[N:4][C:3]=1[O:10][CH3:11]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 585395103-Bromo-5-bromomethyl-2-methoxy-pyridine

Product 1

HCID 585393925-Bromo-6-methoxy-3-pyridineacetonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To 3-bromo-5-bromomethyl-2-methoxy-pyridine (1.42 g, 5.05 mmol) in EtOH (14 mL) and H2O (1.5 mL) was added sodium cyanide (0.25 g, 5.05 mmol), and the reaction was stirred at 50° C. overnight. The mixture was cooled to room temperature and worked up with CH2Cl2 and saturated aqueous NaHCO3. The combined organic layers were dried, filtered, and concentrated to give (5-bromo-6-methoxy-pyridin-3-yl)-acetonitrile.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cbbe0b02eed043baa28f70ad3d7e3a7f
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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