Tetrahydrofuran → 2-(6-Methoxynaphthyl)anthracene

HRID 278835

Reaction equation

HRID 278835 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9](Br)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH2:17]1[CH2:21][O:20][CH2:19][CH2:18]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:19][O:20][C:21]1[CH:4]=[C:3]2[C:8](=[CH:18][CH:17]=1)[C:9]([C:13]1[CH:12]=[CH:11][C:10]3[C:15](=[CH:2][C:3]4[C:8]([CH:9]=3)=[CH:7][CH:6]=[CH:5][CH:4]=4)[CH:14]=1)=[CH:10][CH:15]=[CH:2]2

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 682269,10-Dibromoanthracene

Product 1

HCID 867578972-(6-Methoxynaphthyl)anthraceneYield 82%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

9,10-Dibromoanthracene (23.63 g, 70.3 mmol), 300 mL of THF and a catalytic amount of dichlorobis(triphenylphosphine)palladium (II) were all placed under nitrogen in a round bottomed flask. The Grignard reagent prepared above was then added via a double-end needle transfer while still warm. After the addition, the reaction mixture was allowed to reflux overnight. After cooling to room temperature, the precipitated solid was collected by vacuum filtration and washed with ether, THF, and water. The collected solid was placed into a beaker and HCl (6M) was added followed by ethanol. This mixture is stirred for 60 minutes and the solid is again collected by vacuum filtration. The product was washed until the washings are neutral. After drying, the solid is refluxed gently in CH2Cl2 for 60 minutes. The pure product was filtered and dried to give 85.2 g solid (82% yield) (AA8790-34). 1H NMR (CDCl3) δ(ppm): 3.97 (s, 6H), 7.29 (dd, J1=8.9 Hz, J2=2.4 Hz, 2H), 7.40 (d, J=6.9 Hz 2H), 7.41 (d, J=6.9 Hz, 2H), 7.53 (d, J=2.2 Hz, 2H), 7.57 (d, J=8.0 Hz, 2H), 7.64 (d, J=6.8 Hz, 2H), 7.65 (d, J=6.8 Hz, 2H), 7.94 (d, J=9 Hz, 2H), 7.97 (s, 2H), 8.10 (d, J=8.4 Hz, 2H);. FD-MS: m/z 490 (M+).

Workup

  1. customall placed under nitrogen in a round bottomed flask
  2. additionwas then added via a double-end needle transfer
  3. temperaturewhile still warm
  4. additionAfter the addition
  5. temperatureto reflux overnight
  6. filtrationthe precipitated solid was collected by vacuum filtration
  7. washwashed with ether, THF, and water
  8. additionwas added
  9. filtrationthe solid is again collected by vacuum filtration
  10. washThe product was washed until the washings
  11. customAfter drying
  12. temperaturethe solid is refluxed gently in CH2Cl2 for 60 minutes
  13. filtrationThe pure product was filtered
  14. customdried

Sources & evidence

ORD record
ord-b8f3e5c8a39146289faad3420b49a8d6
Source dataset
uspto-grants-2002_03
Patent number
US06361887B1

Linked notes

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