Sodium Cyanide → HCID 69303601, compound

HRID 746831Notes

Reaction equation

HRID 746831 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[C:4](F)[CH:3]=1.[C-:15]#[N:16].[Na+]>CS(C)=O.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[C:4]([CH:3]=1)[C:15]#[N:16]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 49761822HCID 49761822, compound

Product 1

HCID 69303601HCID 69303601, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

2-(4-Bromo-2-fluorophenyl)pyridine (1.0 g, 3.9 mmol) and sodium cyanide (214 mg, 4.3 mmol) were combined in DMSO (20 mL) under argon. The reaction mixture was heated at 180° C. overnight. TLC analysis showed no starting material present. The reaction mixture was diluted with EtOAc (100 mL), and washed with H2O (3×100 mL), brine (100 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford a dark oil. The crude product was purified by column chromatography eluting with 1:9 EtOAc:Hexane. to afford 5-bromo-2-pyridin-2-ylbenzonitrile (800 mg, 80%). MS 262.1 (M++H).

Workup

  1. washwashed with H2O (3×100 mL), brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto afford a dark oil
  6. customThe crude product was purified by column chromatography
  7. washeluting with 1:9 EtOAc

Sources & evidence

ORD record
ord-368dba4485c441419b601c71524c1503
Source dataset
uspto-grants-2008_07
Patent number
US07393959B2

Reaction notes

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