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

HRID 2277341Notes

Reaction equation

HRID 2277341 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-ae2392788b8e43adb5b907c1dc0762a6
Source dataset
uspto-grants-2015_09
Patent number
US09133119B2

Reaction notes

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