Sodium Chloride → 4-Bromo-7-hydroxy-1-indanone

HRID 1802662Notes

Reaction equation

HRID 1802662 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[Cl-].[Na+].C([O:11][C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)(=O)C=C>O>[Br:18][C:15]1[CH:14]=[CH:13][C:12]([OH:11])=[C:17]2[C:16]=1[CH2:14][CH2:13][C:12]2=[O:11]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 6451240Aluminum(III) ChlorideHCID 137742174-Bromophenyl acrylate

Product 1

HCID 37180504-Bromo-7-hydroxy-1-indanoneYield 66.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of aluminum trichloride (120 g) and sodium chloride (40 g) heated to 100° C. was added 4-bromophenyl acrylate (10.5 g, 50.7 mmol), and the mixture was stirred for 15 min. Then, the mixture was heated to 140° C., and the mixture was stirred for 45 min. The mixture was poured into ice-cooled water and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80) and recrystallized (ethyl acetate/hexane) to give the title compound (3.82 g, yield 36%).

Workup

  1. temperatureThen, the mixture was heated to 140° C.
  2. stirringthe mixture was stirred for 45 min
  3. additionThe mixture was poured into ice-
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80)
  9. customrecrystallized (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d7c8afd3250a417aa54f1d64fb1e5a42
Source dataset
uspto-grants-2013_01
Patent number
US08349879B2

Reaction notes

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