Sodium Iodide → 2,7-Dibromo-9-(2,5-dimethylphenyl)-9-[4-(3,7-dimethyloctyloxy)phenyl]-fluorene

HRID 480996

Reaction equation

HRID 480996 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([C:23]3[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=3[CH3:30])([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[C:4]=2[CH:3]=1.[CH3:31][CH:32]([CH2:36][CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[CH2:33][CH2:34]Cl.[OH-].[K+].[Na+].[I-]>C(OCC)(=O)C.C(O)C>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([C:23]3[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=3[CH3:30])([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH2:34][CH2:33][CH:32]([CH3:31])[CH2:36][CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])=[CH:20][CH:21]=3)[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 14797Potassium HydroxideHCID 2273601-Chloro-3,7-dimethyloctaneHCID 187668472,7-Dibromo-9-(2,5-dimethylphenyl)-9-(4-hydroxyphenyl)fluorene

Product 1

HCID 187668422,7-Dibromo-9-(2,5-dimethylphenyl)-9-[4-(3,7-dimethyloctyloxy)phenyl]-fluorene

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

52 g of 2,7-dibromo-9-(2,5-dimethylphenyl)-9-(4-hydroxyphenyl)fluorene were refluxed with 18 g of 3,7-dimethyloctyl chloride, 80 ml of ethanol, 7 g of KOH and 1 g of NaI for 5 days. According to TLC, the reaction was complete after this time. The solvent was stripped off, ethyl acetate was added, and the precipitate was filtered off with suction and rinsed a number of times with ethyl acetate. The organic phase was dried, and the solvent was stripped off.

Workup

  1. filtrationthe precipitate was filtered off with suction
  2. washrinsed a number of times with ethyl acetate
  3. customThe organic phase was dried

Sources & evidence

ORD record
ord-6d04b460c8404279aa774d3bf11f9768
Source dataset
uspto-grants-2003_11
Patent number
US06653438B1

Linked notes

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