1-Bromooctane → 2,6-dibromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene
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.C(Br)CCCCCCC.[OH-].[Na+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.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]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
2,6-dibromo-4H-cyclopenta[def]phenanthrene (2.6 g, 7.7 mmol) and octyl bromide (3.6 g, 18.5 mmol) in a 50 ml round bottom flask were dissolved with toluene (10 ml), and TBAB (tetrabutylammoniumbromide) (0.125 g, 0.385 mmol) was added thereto. A solution of NaOH (3.1 g, 77 mmol) in water (50 ml) was added to the reaction mixture, and the resultant solution was refluxed for two days. After the reaction was terminated, the reaction solution was extracted with chloroform. The organic layer was dried over MgSO4, concentrated, and purified by silica gel column chromatography (eluent: n-hexane). The eluate was distilled under a reduced pressure to remove unreacted octyl bromide, thereby giving a compound 2 (3.6 g, 80%).
Workup
- additionwas added
- customAfter the reaction was terminated
- extractionthe reaction solution was extracted with chloroform
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated
- custompurified by silica gel column chromatography (eluent: n-hexane)
- distillationThe eluate was distilled under a reduced pressure
- customto remove unreacted octyl bromide
Sources & evidence
- ORD record
- ord-240ebeb48bc3432da84880e48bbb18c1
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329953B2
Reaction notes
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