Boron tribromide → 9,9-Dioctyl-2-hydroxy-7-(4-Nonylphenyl)fluorene

HRID 1243259Notes

Reaction equation

HRID 1243259 reaction equation
B(Br)(Br)Br.[CH2:5]([C:13]1([CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[C:25]2[CH:24]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:28][CH:27]=3)[CH:22]=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][C:16]([O:41]CCCCCCCC)=[CH:17][CH:18]=2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>ClCCl>[CH2:50]([C:13]1([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:14]2[CH:15]=[C:16]([OH:41])[CH:17]=[CH:18][C:19]=2[C:20]2[C:25]1=[CH:24][C:23]([C:26]1[CH:27]=[CH:28][C:29]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:30][CH:31]=1)=[CH:22][CH:21]=2)[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 219245159,9-Dioctyl-2-(4-nonylphenyl)-7-octyloxyfluorene

Product 1

HCID 219245079,9-Dioctyl-2-hydroxy-7-(4-Nonylphenyl)fluorene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1 M solution of boron tribromide in dichloromethane, (0.55 cm3, 0.00581 mol) was added dropwise to a stirred solution of 9,9-dioctyl-2-(4-nonylphenyl)-7-octyloxyfluorene (2.79 g, 0.00388 mol) and dichloromethane (100 cm3) at 0° C. The temperature was allowed to rise to RT overnight and the solution added to ice-water (200 cm3) with vigorous stirring. The product was extracted into diethyl ether (2×200 cm3). The combined organic extracts were washed with saturated aqueous sodium carbonate solution (150 cm3), dried (MgSO4), filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography [silica gel, dichloromethane:hexane: 20:80] (yield 2.2 g, 93.4%).

Workup

  1. extractionThe product was extracted into diethyl ether (2×200 cm3)
  2. washThe combined organic extracts were washed with saturated aqueous sodium carbonate solution (150 cm3)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe residue was purified by column chromatography [silica gel, dichloromethane:hexane: 20:80] (yield 2.2 g, 93.4%)

Sources & evidence

ORD record
ord-6c1cc725377f4d079ac087e05b310c37
Source dataset
uspto-grants-2006_10
Patent number
US07118787B2

Reaction notes

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