Water → 9-Phenanthrenecarbonitrile, 2,3,6,7-tetramethoxy-

HRID 1861580Notes

Reaction equation

HRID 1861580 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].B(F)(F)F.CCOCC.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.O>ClCCl>[CH3:24][O:23][C:17]1[C:18]([O:21][CH3:22])=[CH:19][C:20]2[C:6]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[CH:7]=3)[C:11]([C:12]#[N:13])=[CH:14][C:15]=2[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 2852492HCID 2852492, compoundHCID 178418287HCID 178418287, compound2×

Product 1

HCID 120775929-Phenanthrenecarbonitrile, 2,3,6,7-tetramethoxy-Yield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2,3-Bis-(3,4-dimethoxy-phenyl)-acrylonitile (1.83 g, 5.63 mmol) was dissolved in absolute dichloromethane (100 ml) and the obtained solution was cooled to 0° C. and maintained under nitrogen atmosphere. Boron trifluoride etherate (1.76 g, 12.39 mmol) was dropwise added (within 15 min) to the reaction mixture which was stirred for further 15 min at 0° C. At this temperature, pyridinium chlorochromate (PCC) (2.43 g, 11.26 mmol), was portionwise added (10 portions, 1 portion/min) to the reaction mixture which turned green-brown. After complete addition of PCC, the reaction mixture was stirred for further 10 min, poured into water (200 ml), and extracted with dichloromethane (2×200 ml). The combined organic extracts were dried over magnesium sulphate and evaporated under reduced pressure. The obtained brown residue was chromatographed on silica (CH2Cl2). This afford a yellow material which was further purified by crystallisation in ethanol/dichloromethane: 9/1 to give 2,3,6,7-tetramethoxy-phenanthrene-9-carbonitrile as white powder (yield 1.75 g, 96%).

Workup

  1. temperaturemaintained under nitrogen atmosphere
  2. stirringthe reaction mixture was stirred for further 10 min
  3. extractionextracted with dichloromethane (2×200 ml)
  4. dry with materialThe combined organic extracts were dried over magnesium sulphate
  5. customevaporated under reduced pressure
  6. customThe obtained brown residue was chromatographed on silica (CH2Cl2)
  7. customThis afford a yellow material which
  8. customwas further purified by crystallisation in ethanol/dichloromethane

Sources & evidence

ORD record
ord-3177ba09045c403b880d8de9792b1d03
Source dataset
uspto-grants-2003_03
Patent number
US06534135B1

Reaction notes

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