1-Bromooctane → 2-Bromo-9,9-dioctyl-7-octyloxyfluorene

HRID 1243257Notes

Reaction equation

HRID 1243257 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([OH:15])=[CH:9][CH:10]=3)[C:5]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:4]=2[CH:3]=1.Br[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([O:15][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:9][CH:10]=3)[C:5]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 219245182-Bromo-9,9-dioctyl-7-hydroxyfluorene

Product 1

HCID 219245022-Bromo-9,9-dioctyl-7-octyloxyfluorene

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2-bromo-9,9-dioctyl-7-hydroxyfluorene (6.00 g, 0.0124 mol), 1-bromooctane (3.104 g, 0.0161 mol), potassium carbonate (3.41 g, 0.0247 mol) and butanone (100 cm3) was heated under reflux overnight. The cooled mixture was filtered and evaporated down under reduced pressure. The crude product was purified by column chromatography [silica gel, dichloromethane: hexane: 1:1] and then used without further purification (yield 5.04 g, 68.3%), GC: 99%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. filtrationThe cooled mixture was filtered
  4. customevaporated down under reduced pressure
  5. customThe crude product was purified by column chromatography [silica gel, dichloromethane: hexane: 1:1]
  6. customused without further purification (yield 5.04 g, 68.3%), GC

Sources & evidence

ORD record
ord-30d7a6aadb674e8bb5ad1012c85690e2
Source dataset
uspto-grants-2006_10
Patent number
US07118787B2

Reaction notes

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