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

HRID 254128

Reaction equation

HRID 254128 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>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

4

Reactant 2

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

Product 1

HCID 125243632-bromo-8,9-dihydro-4H-cyclopenta[def]phenanthreneYield 83.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

8,9-dihydro-4H-cyclopenta[def]phenanthrene (4.0 g, 20.8 mmol) was put into a 250 ml round bottom flask (RBF), and CCl4 (100 ml) was added thereto. The reaction mixture was cooled to 0° C., and Br2 (3.3 g, 20.8 mmol) was dropwise added thereto. The reaction solution was incubated for 4 hours and a 10% NaSO3 solution was added thereto. The organic phase was separated, concentrated under a reduced pressure, and recrystallized from n-hexane to obtain 4.7 g of a 2-bromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene compound.

Workup

  1. customThe organic phase was separated
  2. concentrationconcentrated under a reduced pressure
  3. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-59c6361377d046c5afbbdd3118e3e552
Source dataset
uspto-grants-2011_01
Patent number
US07875367B2

Linked notes

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