Bromine → 2-bromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene

HRID 2205267Notes

Reaction equation

HRID 2205267 reaction equation
[CH:1]1[C:14]2[CH2:13][CH2:12][C:11]3[CH:10]=[CH:9][CH:8]=[C:7]4[CH2:15][C:4]([C:5]=2[C:6]=34)=[CH:3][CH:2]=1.[Br:16]Br.[O-]S([O-])=O.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:16][C:2]1[CH:3]=[C:4]2[CH2:15][C:7]3[C:6]4[C:5]2=[C:14]([CH2:13][CH2:12][C:11]=4[CH:10]=[CH:9][CH:8]=3)[CH:1]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24437Sodium SulfiteHCID 6057498,9-Dihydrocyclopenta[def]phenanthrene

Product 1

HCID 125243632-bromo-8,9-dihydro-4H-cyclopenta[def]phenanthreneYield 80.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

8.5 g (44.2 mmol) of 8,9-dihydro-4H-cyclopenta[def]phenanthrene was dissolved in 80 ml of CCl4, and 7.1 g (44.2 mmol) of Br2 was then slowly added thereto at 0° C. The reaction solution was stirred at room temperature for 4 hours and a 10% Na2SO3 solution was added thereto to separate the organic layer. The obtained organic layer was dried with magnesium sulfate, the solvent was evaporated therefrom, and the resultant product was recrystallized with n-hexane. As a result, 9.6 g of the target material was obtained (yield: 80%). The obtained compound was confirmed by LC-MS.

Workup

  1. customat 0° C
  2. customto separate the organic layer
  3. dry with materialThe obtained organic layer was dried with magnesium sulfate
  4. customthe solvent was evaporated
  5. customthe resultant product was recrystallized with n-hexane

Sources & evidence

ORD record
ord-22f72b8d5ffb481a8c11920f941fa040
Source dataset
uspto-grants-2016_06
Patent number
US09371270B2

Reaction notes

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