Sodium Carbonate → 3-(4-Iodo-phenyl)-9-phenyl-9H-carbazole

HRID 1530740노트

반응식

HRID 1530740 반응식
[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][C:16](B4OC(C)(C)C(C)(C)O4)=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:29][C:30]1[CH:35]=[CH:34][C:33](Br)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[I:29][C:30]1[CH:35]=[CH:34][C:33]([C:16]2[CH:17]=[CH:18][C:19]3[N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:8]4[C:13]([C:14]=3[CH:15]=2)=[CH:12][CH:11]=[CH:10][CH:9]=4)=[CH:32][CH:31]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 574156959-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole

생성물 1

HCID 667163243-(4-Iodo-phenyl)-9-phenyl-9H-carbazole

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

90 g (244 mmol) 9-Phenyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-carbazole and 69 g (244 mmol) 1-Iodo-4-Brombenzene [589-87-7] are dissolved in 500 ml toluene treated with 200 ml of a 2 M solution of sodium carbonate. The reaction mixture is carefully degassed and 200 mg tetrakistriphenylphosphine palladiume are added. The reaction is heated to reflux for 20 h. The solution is then cooled to room temperature and the layers are separated. The water phase is extracted three times with toluene, and then the organic layers is washed twice with water dried over magnesium sulphate, filtrated and the solvent is removed in the vacuum. The residue is recrystallized from DMF, to yield 100 g (225 mmol) (92%) of a with powder with a purity of 98.7%.

후처리

  1. customThe reaction mixture is carefully degassed
  2. addition200 mg tetrakistriphenylphosphine palladiume are added
  3. temperatureThe reaction is heated
  4. temperatureto reflux for 20 h
  5. customthe layers are separated
  6. extractionThe water phase is extracted three times with toluene
  7. washthe organic layers is washed twice with water
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltrated
  10. customthe solvent is removed in the vacuum
  11. customThe residue is recrystallized from DMF
  12. customto yield 100 g (225 mmol) (92%) of a with powder with a purity of 98.7%

출처 및 근거

ORD 기록
ord-fd878b1bda654024b0ef616de71ff471
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09093656B2

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