N-bromobutanimide → HCID 22227132, compound

HRID 1745871Notes

Reaction equation

HRID 1745871 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[CH2:11][CH:10]=[CH:9]2)([CH3:3])[CH3:2].[Br:13]N1C(=O)CCC1=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CS(C)=O.C(OCC)C.O>[CH:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[CH2:11][C:10]([Br:13])=[CH:9]2)([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 67184N-bromobutanimideHCID 521998p-Toluenesulfonic acid monohydrateHCID 22227113HCID 22227113, compound

Product 1

HCID 22227132HCID 22227132, compoundYield 97.3%

Reagents, catalysts & solvents 3

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

Procedure

Using a 200 ml Erlenmeyer flask as the reactor, 7.00 g (44.20 millimoles) of 7-isopropylindene was dissolved in a mixed solvent of 0.91 g (106.08 millimoles) of distilled water and 60 ml of dimethyl sulfoxide. To this reaction solution there was added 9.44 g (53.03 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 70 ml of toluene. To this solution there was added 0.84 g (4.42 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 10.2 g of 7-isopropyl-2-bromo-indene as a reddish brown oil (97% yield).

Workup

  1. temperaturewhile cooling on ice
  2. temperaturewhile cooling on ice, extraction
  3. washthe extract was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration of the magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. dissolutiondissolved in 70 ml of toluene
  8. temperaturethe mixture was heated
  9. temperatureto reflux for 4 hours
  10. temperatureAfter reflux
  11. customhydrolysis
  12. temperaturewhile cooling on ice, and extraction
  13. washThe extract was washed once with a saturated sodium bicarbonate aqueous solution
  14. washwashed once with saturated saline
  15. dry with materialdried over anhydrous magnesium sulfate
  16. customAfter drying
  17. filtrationthe magnesium sulfate was filtered off
  18. distillationthe solvent was distilled off under reduced pressure, and purification

Sources & evidence

ORD record
ord-cab2ec70033546158e48dfb1c264ad1b
Source dataset
uspto-grants-2006_03
Patent number
US07019157B2

Reaction notes

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