Sodium Cyanide → HCID 22930026, compound

HRID 1295940Notes

Reaction equation

HRID 1295940 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1Br.[C:14]([Cu])#[N:15].[C-:17]#[N:18].[Na+]>CN(C)C=O.O>[F:12][C:4]1[C:5]([O:10][CH3:11])=[C:6]([O:8][CH3:9])[CH:7]=[C:2]([C:17]#[N:18])[C:3]=1[C:14]#[N:15]

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 22929662HCID 22929662, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 22930026HCID 22930026, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

After dissolving the 1,2-dibromo-3-fluoro-4,5-dimethoxybenzene (40 g, 0.127 mol) in dimethylformamide (300 ml), CuCN (34.1 g, 0.381 mol) was added at room temperature while stirring and the mixture was stirred at 150° C. for 4 hours. After cooling on ice, a solution of sodium cyanide (44 g) in water (600 ml) was added and the mixture was stirred at room temperature for 10 minutes, after which extraction was performed with ethyl acetate (500 ml×3) and then after washing the combined organic layers with brine (500 ml) and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (white crystals 12.0 g, 46%).

Workup

  1. additionwas added at room temperature
  2. stirringthe mixture was stirred at 150° C. for 4 hours
  3. temperatureAfter cooling on ice
  4. stirringthe mixture was stirred at room temperature for 10 minutes
  5. extractionafter which extraction
  6. washafter washing the combined organic layers with brine (500 ml)
  7. dry with materialdrying over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-ef9667c17aeb43c8a6dd86e983b1a0ed
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

Loading…