Pyridinium chloride → 8-bromo-6H-dibenzo[c,h]-chromen-2-ol

HRID 1751528Notes

Reaction equation

HRID 1751528 reaction equation
Cl.N1C=CC=CC=1.[Br:8][C:9]1[CH:10]=[CH:11][C:12]2[C:21]3[C:16](=[C:17]4[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][C:18]4=[CH:19][CH:20]=3)[O:15][CH2:14][C:13]=2[CH:28]=1>O>[Br:8][C:9]1[CH:10]=[CH:11][C:12]2[C:21]3[C:16](=[C:17]4[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][C:18]4=[CH:19][CH:20]=3)[O:15][CH2:14][C:13]=2[CH:28]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 596108178-bromo-2-methoxy-6H-dibenzo[c,h]chromene

Product 1

HCID 596110238-bromo-6H-dibenzo[c,h]-chromen-2-olYield 56.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

Pyridine hydrochloride (4.4 g, 37.8 mmol) was heated to 190° C. 8-bromo-2-methoxy-6H-dibenzo[c,h]chromene (1.29 g, 3.8 mmol) was added and the reaction was stirred at 190° C. After four hours, the reaction was cooled to room temperature and diluted with water. A precipitate formed which was collected by filtration and purified by flash column chromatography to yield 8-bromo-6H-dibenzo[c,h]-chromen-2-ol (697 mg, 56%).

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. customA precipitate formed which
  3. filtrationwas collected by filtration
  4. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-74eb8abb39a04aaa86b4e293beb7ac91
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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