Water → 6-Bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridine

HRID 2277341노트

반응식

HRID 2277341 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21](O)([CH3:23])[CH3:22])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.CS(O)(=O)=O.O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]3=[C:13]([C:12]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[N:6]3[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]2([CH3:23])[CH3:22])[CH:14]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 672027742-[2-(3-Bromocarbazol-9-yl)phenyl]propan-2-ol

생성물 1

HCID 671097356-Bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridine

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
60 °C

실험 절차

16.3 g (44 mmol) of 2-[2-(3-bromocarbazol-9-yl)phenyl]propan-2-ol are dissolved in 1200 ml of degassed toluene, a suspension of 40 g of polyphosphoric acid and 28 ml of methanesulfonic acid is added, and the mixture is heated at 60° C. for 1 h. The batch is cooled, and water is added. A solid precipitates out and is dissolved in CH2Cl2/THF (1:1). The solution is carefully rendered alkaline using 20% NaOH, and the phases are separated and dried over MgSO4. The solid obtained is washed by stirring with heptane. Yield: 13.5 g (37 mmol), 87% of theory, purity according to 1H-NMR about 95%.

후처리

  1. additionis added
  2. temperatureThe batch is cooled
  3. customA solid precipitates out and
  4. dissolutionis dissolved in CH2Cl2/THF (1:1)
  5. customthe phases are separated
  6. dry with materialdried over MgSO4
  7. customThe solid obtained
  8. washis washed

출처 및 근거

ORD 기록
ord-ae2392788b8e43adb5b907c1dc0762a6
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133119B2

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