Potassium Cyanide → HCID 68582824, compound

HRID 2234741Notes

Reaction equation

HRID 2234741 reaction equation
Br[C:2]1[C:14]([O:15][CH3:16])=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=3)[C:5]([CH2:21][CH2:22][CH3:23])([CH2:18][CH2:19][CH3:20])[C:4]=2[CH:3]=1.[Cu][C:25]#[N:26].[C-:27]#[N:28].[K+]>CN(C)C=O.O>[C:27]([C:2]1[C:14]([O:15][CH3:16])=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([C:25]#[N:26])=[CH:9][CH:10]=3)[C:5]([CH2:21][CH2:22][CH3:23])([CH2:18][CH2:19][CH3:20])[C:4]=2[CH:3]=1)#[N:28]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 59297263HCID 59297263, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 68582824HCID 68582824, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,7-dibromo-9,9-dipropyl-3-methoxyfluorene (83 g, 0.19 mol), and copper(I) cyanide (50 g, 0.56 mol) in anhydrous dimethylformamide (70.0 mL) was stirred under reflux and argon for 18 hours. The reaction was allowed to cool to 90° C. and treated with a solution of potassium cyanide (100 g) in water (350 mL). The resulting mixture was stirred rapidly for a further 4.5 hours. The granular product was collected by filtration, crushed, washed with water and dried. The tan colored solid was extracted from a soxhlet with methylcyclohexane. Cooling and seeding of the methylcyclohexane extract afforded 2,7-dicyano-9,9-dipropyl-3-methoxyfluorene upon filtration (62.6 g; yield 99%).

Workup

  1. temperatureunder reflux
  2. stirringThe resulting mixture was stirred rapidly for a further 4.5 hours
  3. filtrationThe granular product was collected by filtration
  4. customcrushed
  5. washwashed with water
  6. customdried
  7. extractionThe tan colored solid was extracted from a soxhlet with methylcyclohexane
  8. temperatureCooling
  9. extractionseeding of the methylcyclohexane extract

Sources & evidence

ORD record
ord-0018f3bea6954ab9acfdd847b711e9d0
Source dataset
uspto-grants-2010_05
Patent number
US07713452B2

Reaction notes

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