Benzyl Bromide → HCID 12389274, compound

HRID 1438865Notes

Reaction equation

HRID 1438865 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(C)=O>[CH2:23]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:6][CH:7]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7498Benzyl Bromide2×HCID 11430Potassium Carbonate2×HCID 112872602-(4-Hydroxyphenyl)indole

Product 1

HCID 12389274HCID 12389274, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

While stirring and under nitrogen, a mixture of 3.14 g (0.15 mol) of 2-(4'-hydroxy-phenyl)-indole, prepared as in Example 2, 2.1 g of anhydrous potassium carbonate and 100 ml of anhydrous acetone was refluxed and a solution of 50 ml of anhydrous acetone containing 1.8 ml (0.015 mol) of benzyl bromide was then added, drop-by-drop. The solution was heated for 4 hours and 0.4 ml (0.003 mole) of benzyl bromide was added with 0.5 g of potassium carbonate. Heating was continued for 4 hours and the hot solution was filtered. The filter was washed with 50 ml of acetone, the filtrate was concentrated under vacuum and was taken up in 100 ml of boiling methylethylketone. The hot reaction medium was filtered and the filtrate was cooled in an ice-bath for 30 minutes. The precipitate which was obtained was centrifuged and recrystallized from methylethylketone to give 3.3 g of 2-(4'-benzyloxy-phenyl)-indole.

Workup

  1. temperaturewas refluxed
  2. temperatureThe solution was heated for 4 hours
  3. temperatureHeating
  4. filtrationthe hot solution was filtered
  5. washThe filter was washed with 50 ml of acetone
  6. concentrationthe filtrate was concentrated under vacuum
  7. filtrationThe hot reaction medium was filtered
  8. temperaturethe filtrate was cooled in an ice-bath for 30 minutes
  9. customThe precipitate which was obtained
  10. customrecrystallized from methylethylketone

Sources & evidence

ORD record
ord-611fa16454fc4ecc9b0590bb8c799b3b
Source dataset
uspto-grants-1977_11
Patent number
US04057530

Reaction notes

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