N-bromobutanimide → HCID 67328501, compound

HRID 1257558Notes

Reaction equation

HRID 1257558 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:13]2[C:21]([CH3:22])=[CH:20][CH:19]=[C:18]3[C:14]=2[CH:15]=[CH:16][CH2:17]3)[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:3])[CH3:2].[Br:23]N1C(=O)CCC1=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CS(C)=O.O.C1(C)C=CC=CC=1>[Br:23][C:16]1[CH2:17][C:18]2[C:14]([CH:15]=1)=[C:13]([C:6]1[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=1)[C:21]([CH3:22])=[CH:20][CH:19]=2

Participants

7

Reactant 3

HCID 67184N-bromobutanimideHCID 521998p-Toluenesulfonic acid monohydrateHCID 86657856HCID 86657856, compound

Product 1

HCID 67328501HCID 67328501, compoundYield 101.8%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

The obtained 4-(3,5-diisopropylphenyl)-5-methylindene (4.69 g, 15.9 mmol) was dissolved in dimethylsulfoxide (40 mL), and water (1.1 g) was added. N-Bromosuccinimide (NBS)(3.1 g, 17.5 mmol) was added at 5 to 10° C., and after elevating the temperature naturally, reaction solution was stirred for 1 hour at room temperature. Reaction solution was slowly added to mixed solution of toluene and water at room temperature, then, aqueous phase was separated. Organic layer was washed with diluted hydrochloric acid, and after aqueous phase was removed, p-toluene sulfonic acid mono hydrate (0.43 g, 2.3 mmol) was added. After reacting for 1.5 hours while heating under reflux, reaction solution was washed with aqueous solution of sodium hydroxide (1N) and water, and organic layer was extracted. Organic layer was dried over magnesium sulfate, then, solvent was distilled off under reduced pressure to obtain the crude product (5.98 g).

Workup

  1. customreaction solution
  2. customReaction solution
  3. additionwas slowly added
  4. customaqueous phase was separated
  5. washOrganic layer was washed with diluted hydrochloric acid
  6. customafter aqueous phase was removed
  7. waitAfter reacting for 1.5 hours
  8. temperaturewhile heating
  9. temperatureunder reflux
  10. customreaction solution
  11. washwas washed with aqueous solution of sodium hydroxide (1N) and water, and organic layer
  12. extractionwas extracted
  13. dry with materialOrganic layer was dried over magnesium sulfate
  14. distillationsolvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4a255879792840f2be7ae6650b880eec
Source dataset
uspto-grants-2013_06
Patent number
US08461365B2

Reaction notes

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