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1,6-Dibromohexane → 2,7-Dibromo-9,9-bis(6-bromohexyl)-9H-fluorene

HRID 514168
Notes
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Reaction equation

HRID 514168 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)[CH2:5][C:4]=2[CH:3]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][Br:23].[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[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]([CH2:10][CH2:11][CH2:12][CH2:4][CH2:3][CH2:2][Br:1])([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][Br:23])[C:4]=2[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 123681,6-DibromohexaneHCID 14797Potassium HydroxideHCID 1400732,7-Dibromofluorene

Product 1

HCID 218679302,7-Dibromo-9,9-bis(6-bromohexyl)-9H-fluoreneYield 56.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalyst
HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1 (5.0 g, 15.43 mmol), 1,6-dibromohexane (30 mL), tetrabutylammonium bromide (TBAB) (0.5 g), and potassium hydroxide aqueous solution (30 mL, 50% w/w) was stirred at 70° C. for 24 h under nitrogen. After diluting the reaction mixture with dichloromethane, the organic layer was washed with water and brine. The separated organic layer was dried over magnesium sulfate, and dichloromethane was evaporated. The residual 1,6-dibromohexane was distilled in a vacuum, and compound 2 (5.67 g, 56.5%) was obtained as a white crystal by chromatography with hexane/CH2Cl2 (95:5) as the eluent; m.p. 68° C. 1H NMR (500 MHz, CDCl3). δ (ppm): 7.51 (d, 2H, J=8.0 Hz), 7.45 (d, 2H, J=8.0 Hz), 7.42 (s, 2H), 3.27 (t, 4H, J=7 Hz), 1.91 (t, 4H, J=8.5 Hz), 1.65 (p, 4H, J=8 Hz), 1.18 (p, 4H, J=8 Hz), 1.06 (p, 4H, J=7.5 Hz), 0.57 (m, 4H).

Workup

  1. washthe organic layer was washed with water and brine
  2. dry with materialThe separated organic layer was dried over magnesium sulfate, and dichloromethane
  3. customwas evaporated
  4. distillationThe residual 1,6-dibromohexane was distilled in a vacuum

Sources & evidence

ORD record
ord-0a2e70d02b8142bc9d4e1b53a944a2c9
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09105851B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes