Phenol → 2,7-Dibromo-9-(2,5-dimethylphenyl)-9-(4-hydroxyphenyl)fluorene

HRID 480995Notes

Reaction equation

HRID 480995 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:8][C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][C:15]([Br:22])=[CH:16][CH:17]=3)[C:12]([C:24]3[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=3[CH3:31])(O)[C:11]=2[CH:10]=1.SC(C)C(O)=O.S(=O)(=O)(O)O>O.CO.C1(C)C=CC=CC=1>[Br:8][C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][C:15]([Br:22])=[CH:16][CH:17]=3)[C:12]([C:24]3[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=3[CH3:31])([C:4]3[CH:5]=[CH:6][C:1]([OH:7])=[CH:2][CH:3]=3)[C:11]=2[CH:10]=1

Participants

8

Reactant 4

HCID 996PhenolHCID 1118Sulfuric AcidHCID 62326(+-)-2-Mercaptopropionic acidHCID 187668432,7-Dibromo-9-(2,5-dimethylphenyl)-9H-fluoren-9-OL

Product 1

HCID 187668472,7-Dibromo-9-(2,5-dimethylphenyl)-9-(4-hydroxyphenyl)fluorene

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

9.5 g of phenol were mixed with 22.2 g of 2,7-dibromo-9-(2,5-dimethylphenyl)fluoren-9-ol, 25 ml of toluene and 0.1 ml of mercapto-propionic acid. 5 ml of concentrated sulfuric acid were subsequently added dropwise. The batch was then stirred at 60° C. for about 2 hours, and finally 100 ml of MeOH and 100 ml of water were added. The solid was filtered off with suction and further purified by stirring with ethanol.

Workup

  1. filtrationThe solid was filtered off with suction
  2. customfurther purified
  3. stirringby stirring with ethanol

Sources & evidence

ORD record
ord-4e3ca63617244fcb8644a6494c84f657
Source dataset
uspto-grants-2003_11
Patent number
US06653438B1

Reaction notes

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