1-Bromooctane → HCID 68441959, compound

HRID 525978Notes

Reaction equation

HRID 525978 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]3[NH:20][C:21]4[C:26]([C:27]=3[CH:28]=2)=[CH:25][C:24]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:31][CH:30]=2)=[CH:23][CH:22]=4)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Br[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52].[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:45]([N:20]1[C:19]2[CH:18]=[CH:17][C:16]([C:13]3[CH:12]=[CH:11][C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:15][CH:14]=3)=[CH:28][C:27]=2[C:26]2[C:21]1=[CH:22][CH:23]=[C:24]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:31][CH:30]=1)[CH:25]=2)[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]

Participants

6

Reactant 3

HCID 81401-BromooctaneHCID 14798Sodium HydroxideHCID 684414343,6-Bis(4-(octyloxy)phenyl)-carbazole

Product 1

HCID 68441959HCID 68441959, compoundYield 26.7%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

3,6-bis(4-(octyloxy)phenyl)-carbazole (4.2 g, 7.29 mmol), 1-bromooctane (4.25 g, 22.0 mmol) and tetrabutylammoniumhydrogensulphate (0.64 g, 1.88 mmol) was dissolved in toluene and mixed with NaOH 50% aqueous solution (5.5 ml). The reaction was quenched after 4 h, extracted three times with ether, and the combined organic phases was washed with water, evaporated, and purified using column chromatography with a 5/2 petroleum ether/toluene mixture as mobile phase. The product was obtained as colourless oil which crystallized to give 9-octyl-3,6-bis(4-(octyloxy)phenyl)-carbazole (1.34 g, 1.95 mmol) as white crystals. 1H-NMR(C2D2Cl4, δ): 0.7-0.9 (m, 9H), 1.15-1.45 (m, 30H), 1.758 (m, 4H), 1.848 (m, 2H), 3.957 (t, 4H), 4.251 (t, 2H), 6.951 (d, 4H), 7.389 (d, 2H), 7.61 (m, 6H) 8.23 (s, 2H) MS MALDI-TOF (m/z): 687.461

Workup

  1. customThe reaction was quenched after 4 h
  2. extractionextracted three times with ether
  3. washthe combined organic phases was washed with water
  4. customevaporated
  5. custompurified
  6. customThe product was obtained as colourless oil which
  7. customcrystallized

Sources & evidence

ORD record
ord-f09df986c73e4316b2c02fd68a9daf4d
Source dataset
uspto-grants-2016_05
Patent number
US09343198B2

Reaction notes

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