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

HRID 2193975Notes

Reaction equation

HRID 2193975 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.CI>C(Cl)Cl.O.CN(P(N(C)C)(N(C)C)=O)C>[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

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 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 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 12679HexamethylphosphoramideSolvent

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. CH3I (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. customto separate an organic layer
  3. customThe organic layer was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4c1fa51bb4694c1791c82fa1ebe8bd51
Source dataset
uspto-grants-2012_12
Patent number
US08329953B2

Reaction notes

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