Sodium Hydroxide → 2,7-Dibromo-9-(2-ethylhexyl)carbazole

HRID 2244960

반응식

HRID 2244960 반응식
[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)[NH:5][C:4]=2[CH:3]=1.Br[CH2:17][CH:18]([CH2:23][CH3:24])[CH2:19][CH2:20][CH2:21][CH3:22].S.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>CC(C)=O>[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)[N:5]([CH2:17][CH:18]([CH2:23][CH3:24])[CH2:19][CH2:20][CH2:21][CH3:22])[C:4]=2[CH:3]=1

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 868042-Ethylhexyl bromideHCID 111515032,7-DibromocarbazoleHCID 162054371-Butanaminium,N,N,N-tributyl-, sulfide (1:1)

생성물 1

HCID 120705112,7-Dibromo-9-(2-ethylhexyl)carbazole

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of 2,7-dibromocarbazole (3.0 g, 8.95 mmol), 1-bromo-2-ethylhexane (2.70 g, 13.4 mmol), tetra-n-butylammonium hydrogen sulfide (0.1 g), and NaOH (0.54 g, 13.5 mmol) in acetone (30 mL) was refluxed for 9 h. After the reaction, the acetone was removed under vacuum and the residue was extracted with toluene. The combined organic layer was washed with a saturated NaCl aqueous solution, and dried over MgSO4. After removal of the solvent, the residue was purified by column chromatography on silica gel using hexane as the eluent to afford 2,7-dibromo-9-(2-ethylhexyl)-carbazole as a white powder. Yield: 2.46 g (62.9%). M.P.: 95-97° C.

후처리

  1. temperaturewas refluxed for 9 h
  2. customAfter the reaction
  3. customthe acetone was removed under vacuum
  4. extractionthe residue was extracted with toluene
  5. washThe combined organic layer was washed with a saturated NaCl aqueous solution
  6. dry with materialdried over MgSO4
  7. customAfter removal of the solvent
  8. customthe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-4b20a7e3c8ab4988ba23464f0cb0a5ff
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07679082B2

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