Dimethylformamide → 2-(6-Bromopyridin-3-yl)acetonitrile

HRID 889291Notes

Reaction equation

HRID 889291 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[CH3:10][N:11](C=O)C.[C-]#N.[Na+].[Cl-].[NH4+]>C(OCC)(=O)C>[Br:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][C:10]#[N:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 64246582-Bromo-5-(chloromethyl)pyridine

Product 1

HCID 177499762-(6-Bromopyridin-3-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3.75 g (18.2 mmol) of the compound from Example 6A are initially introduced into 20 ml DMF, 979 mg (20.0 mmol) sodium cyanide are added and the mixture is stirred at RT for 2 d. The reaction mixture is introduced on to a mixture of 250 ml saturated ammonium chloride solution and 200 ml ethyl acetate and the aqueous phase is extracted with ethyl acetate (three times with 100 ml each time). The combined organic phases are dried over sodium sulfate, filtered and concentrated and the residue is dried in vacuo. The product obtained in this way is reacted without further purification.

Workup

  1. additionare added
  2. extractionthe aqueous phase is extracted with ethyl acetate (three times with 100 ml each time)
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue is dried in vacuo
  7. customThe product obtained in this way
  8. customis reacted without further purification

Sources & evidence

ORD record
ord-a969a42e32974f22b6062135daa58f5a
Source dataset
uspto-grants-2012_08
Patent number
US08252817B2

Reaction notes

Loading…