Water → HCID 67451857, compound

HRID 1485590Notes

Reaction equation

HRID 1485590 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:12]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)=[C:6]([C:8](O)([CH3:10])[CH3:9])[CH:7]=1.CS(O)(=O)=O.O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:12]3[C:24]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:18]4[CH:17]=[CH:16][CH:15]=[C:14]([C:8]([CH3:10])([CH3:9])[C:6]=2[CH:7]=1)[C:13]3=4

Participants

5

Reactant 3

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 67451391HCID 67451391, compound

Product 1

HCID 67451857HCID 67451857, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

16.4 g (43.6 mmol) of 2-(5-bromo-2-carbazol-9-ylphenyl)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 methylene chloride/THF (1:1). The solution is carefully rendered alkaline using 20% NaOH, the phases are separated and dried over MgSO4. The solid obtained is washed by stirring with heptane. Yield: 14.8 g (40 mmol), 95% 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 methylene chloride/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-6e81af197d21458aad39886f31599b29
Source dataset
uspto-grants-2016_08
Patent number
US09422287B2

Reaction notes

Loading…