Toluene → HCID 18324236, compound

HRID 1251611Notes

Reaction equation

HRID 1251611 reaction equation
[C:1]1([C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][CH:12]([Br:17])[CH:13]3O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>CCOCC>[C:1]1([C:7]2[CH:15]=[C:14]3[C:10](=[CH:9][CH:8]=2)[CH2:11][C:12]([Br:17])=[CH:13]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 18324235HCID 18324235, compound

Product 1

HCID 18324236HCID 18324236, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a one-necked flask of 500 ml, fitted with an dropping funnel and on top of the funnel a condenser, was added 10.19 g (35.2 mmol) of 6-phenyl-2-bromoindanol, 0.671 g (0.10 mol %) p-toluenesulfonic acid and 350 ml of toluene. After 7 hours of refluxing the mixture was diluted with ether and extracted with water and water/NaHCO3. The organic layer was dried over Na2SO4. The Na2SO4 was filtered off and the filtrate was evaporated under reduced pressure. The solid material was dissolved in hot n-pentane and recrystallized giving 7.56 g (27.9 mmol) of 5-phenyl-2-bromoindene. Yield 79%.

Workup

  1. customTo a one-necked flask of 500 ml, fitted with an dropping funnel and on top of the funnel a condenser
  2. temperatureAfter 7 hours of refluxing the mixture
  3. extractionextracted with water and water/NaHCO3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationThe Na2SO4 was filtered off
  6. customthe filtrate was evaporated under reduced pressure
  7. dissolutionThe solid material was dissolved in hot n-pentane
  8. customrecrystallized

Sources & evidence

ORD record
ord-4e3eddb91a7648529ac9d18cd72ebf0f
Source dataset
uspto-grants-2002_01
Patent number
US06342622B1

Reaction notes

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