Dimethyl Sulfoxide → 2,6-dibromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene

HRID 1670163Notes

Reaction equation

HRID 1670163 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]2[CH2:16][C:11]3[C:12]4=[C:13]2[C:4](=[CH:5][CH:6]=[C:7]4[CH:8]=[C:9]([Br:17])[CH:10]=3)[CH:3]=1.CC([O-])(C)C.[K+].CS(C)=O.CN(P(N(C)C)(N(C)C)=O)C>C(Cl)Cl.O>[Br:1][C:2]1[CH:15]=[C:14]2[CH2:16][C:11]3[C:12]4[C:13]2=[C:4]([CH2:5][CH2:6][C:7]=4[CH:8]=[C:9]([Br:17])[CH:10]=3)[CH:3]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 12679HexamethylphosphoramideHCID 23665647Potassium tert-butoxideHCID 594310762,6-dibromo-4H-cyclopenta[def]phenanthrene

Product 1

HCID 125243672,6-dibromo-8,9-dihydro-4H-cyclopenta[def]phenanthreneYield 133.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2,6-dibromo-4H-cyclopenta[def]phenanthrene (2.6 g, 7.7 mmol), t-BuOK (20.8 g, 61.6 mmol), DMSO (20 ml), and HMPA (20 ml) was placed in 50 ml round bottom flask with a syringe. The mixture was stirred for 50 minutes at room temperature and cooled to 0° C. CH3l (3.75 ml, 61.6 mmol) was dropped to the mixture with a syringe and the resultant solution was stirred for 30 minutes at 0° C. Then, water (50 ml) and methylene chloride (50 ml) were added to the solution to separate an organic layer. The organic layer was purified by silica gel column chromatography to obtain compound 2 (3.6 g, 80%). 1H NMR (300 MHz, CDCl3, δ): 7.98(2H, s), 7.79(2H, s), 7.73(2H, s), 1.93(m, 6H).

Workup

  1. temperaturecooled to 0° C
  2. additionCH3l (3.75 ml, 61.6 mmol) was dropped to the mixture with a syringe
  3. customto separate an organic layer
  4. customThe organic layer was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2cdff173bf2b4a92890a3ab49060b296
Source dataset
uspto-grants-2011_08
Patent number
US07990053B2

Reaction notes

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