p-Toluenesulfonic acid → HCID 117770576, compound

HRID 926407Notes

Reaction equation

HRID 926407 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[CH:12]=[CH:13][CH2:14]3)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Br:19]N1C(=O)CCC1=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O.CS(C)=O>[Br:19][C:13]1[CH2:14][C:15]2[C:11]([CH:12]=1)=[C:10]([C:7]1[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=1)[CH:18]=[CH:17][CH:16]=2

Participants

7

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 67184N-bromobutanimideHCID 131735018HCID 131735018, compound

Product 1

HCID 117770576HCID 117770576, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

Into a 500-ml glass reaction vessel, 15.4 g of 4-(4-i-propylphenyl)-indene (67 mmol), 7.2 ml of distilled water and 200 ml of DMSO were added. Then, 17 g (93 mmol) of N-bromosuccinimide was gradually added and the resultant mixture was stirred for 2 hours at room temperature. The reaction liquid was poured into 500 ml of distilled water, and the resultant mixture was extracted with 100 ml of toluene for 3 times. The resultant toluene layer was washed with saturated brine. Then, 2 g (11 mmol) of p-toluenesulfonic acid was added to the washed toluene layer and refluxed under heating while removing water. The reaction liquid was left to cool, washed with saturated brine and dried over sodium sulfate. Then, the sodium sulfate was removed by filtration and the resultant filtrate was evaporated under reduced pressure to remove the solvent. The resultant residue was purified by silica gel column chromatography to thereby obtain 19.8 g of 2-bromo-4-(4-i-propylphenyl)-indene as yellow liquid (yield: 96%).

Workup

  1. additionwere added
  2. customThe reaction liquid
  3. extractionthe resultant mixture was extracted with 100 ml of toluene for 3 times
  4. washThe resultant toluene layer was washed with saturated brine
  5. temperaturerefluxed
  6. temperatureunder heating
  7. customwhile removing water
  8. customThe reaction liquid
  9. waitwas left
  10. temperatureto cool
  11. washwashed with saturated brine
  12. dry with materialdried over sodium sulfate
  13. customThen, the sodium sulfate was removed by filtration
  14. customthe resultant filtrate was evaporated under reduced pressure
  15. customto remove the solvent
  16. customThe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-617edf2848d14cfd9121ebdb1d662155
Source dataset
uspto-grants-2016_03
Patent number
US09284427B2

Reaction notes

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