N-bromobutanimide → HCID 22227144, compound

HRID 1745869Notes

Reaction equation

HRID 1745869 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[CH2:9][CH:8]=[CH:7]2.[Br:11]N1C(=O)CCC1=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CS(C)=O.C(OCC)C.O>[Br:11][C:8]1[CH2:9][C:10]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[CH:3][C:2]=2[Br:1]

Participants

7

Reactant 3

HCID 67184N-bromobutanimideHCID 521998p-Toluenesulfonic acid monohydrateHCID 133302097-Bromo-1H-indene

Product 1

HCID 22227144HCID 22227144, compoundYield 67.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent3×HCID 3283Diethyl EtherSolvent2×

Procedure

Using a 200 ml Erlenmeyer flask, 7.00 g (35.89 millimoles) of 7-bromoindene produced by the method described in J. Org. Chem. 49, 4226–4237(1984) was dissolved in a mixed solvent of 1.42 g (79.00 millimoles) of distilled water and 70 ml of dimethyl sulfoxide. To this reaction solution there was added 7.67 g (43.07 millimoles) of N-bromosuccinimide while cooling on ice, and the mixture was then stirred for one hour at room temperature. After hydrolysis with distilled water while cooling on ice, extraction was performed several times with diethyl ether, and the extract was washed with saturated saline and then dried over anhydrous magnesium sulfate. After filtration of the magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained product was transferred to a 200 ml Erlenmeyer flask and dissolved in 100 ml of toluene. To this solution there was added 0.68 g (3.59 millimoles) of p-toluenesulfonic acid hydrate, and the mixture was heated to reflux for 4 hours. After reflux, hydrolysis was performed with distilled water while cooling on ice, and extraction was performed several times with diethyl ether. The extract was washed once with a saturated sodium bicarbonate aqueous solution, washed once with saturated saline, and then dried over anhydrous magnesium sulfate. After drying, the magnesium sulfate was filtered off, the solvent was distilled off under reduced pressure, and purification was performed with a silica gel column to obtain 6.6 g of 2,7-dibromoindene as white crystals (67% yield).

Workup

  1. customproduced by the method
  2. temperaturewhile cooling on ice
  3. temperaturewhile cooling on ice, extraction
  4. washthe extract was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration of the magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. dissolutiondissolved in 100 ml of toluene
  9. temperaturethe mixture was heated
  10. temperatureto reflux for 4 hours
  11. temperatureAfter reflux
  12. customhydrolysis
  13. temperaturewhile cooling on ice, and extraction
  14. washThe extract was washed once with a saturated sodium bicarbonate aqueous solution
  15. washwashed once with saturated saline
  16. dry with materialdried over anhydrous magnesium sulfate
  17. customAfter drying
  18. filtrationthe magnesium sulfate was filtered off
  19. distillationthe solvent was distilled off under reduced pressure, and purification

Sources & evidence

ORD record
ord-3a9215d85baf427cac56cb1e949ea747
Source dataset
uspto-grants-2006_03
Patent number
US07019157B2

Reaction notes

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