Chlorosulfonic acid → 1-Indanone, 6-bromo-

HRID 1256262Notes

Reaction equation

HRID 1256262 reaction equation
S(Cl)(=O)(=O)O.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:9][CH:8]=1>O>[Br:6][C:7]1[CH:8]=[C:9]2[C:10]([CH2:13][CH2:14][C:15]2=[O:17])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 27356093-(4-Bromophenyl)propionic acid

Product 1

HCID 1397781-Indanone, 6-bromo-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To chlorosulfuric acid (1.19 L) was added 3-(4-bromophenyl)propanoic acid (91.1 g) under ice cooling and the mixture was stirred for 2 hours. To H2O (2.00 L), the reaction mixture was slowly added under ice cooling, and extracted 6 times with CHCl3. The combined organic layers were washed with a saturated aqueous NaHCO3 solution, dried over Na2SO4 and concentrated under reduced pressure. To the resultant residue, MeOH was added and the mixture was heated to reflux for 30 minutes. A solid substance was obtained by filtration to give solid A. The filtrate was concentrated under reduced pressure and solid B was obtained in the same manner. Thereafter, the filtrate was again concentrated under reduced pressure and solid C was obtained in the same manner. Solids A, B and C were combined to obtain 6-bromo-2,3-dihydro-1H-inden-1-one (59.3 g, a light yellow solid).

Workup

  1. extractionextracted 6 times with CHCl3
  2. washThe combined organic layers were washed with a saturated aqueous NaHCO3 solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. additionTo the resultant residue, MeOH was added
  6. temperaturethe mixture was heated
  7. temperatureto reflux for 30 minutes
  8. customA solid substance was obtained by filtration
  9. customto give solid A
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customsolid B was obtained in the same manner
  12. concentrationThereafter, the filtrate was again concentrated under reduced pressure
  13. customsolid C was obtained in the same manner

Sources & evidence

ORD record
ord-52fee74c53cf45a1b8651574e2ef9cc6
Source dataset
uspto-grants-2013_06
Patent number
US08461182B2

Reaction notes

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