Sodium Chloride → 5-Bromo-3-methyl-2,3-dihydro-1h-inden-1-one

HRID 2219809Notes

Reaction equation

HRID 2219809 reaction equation
[Cl-].[Na+].[Cl-].[Al+3].[Cl-].[Cl-].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:19])[CH2:15][CH2:16][CH2:17]Cl)=[CH:10][CH:9]=1>>[Br:7][C:8]1[CH:13]=[C:12]2[C:11](=[CH:10][CH:9]=1)[C:14](=[O:19])[CH2:15][CH:16]2[CH3:17]

Participants

4

Reactant 3

HCID 5234Sodium ChlorideHCID 783174'-Bromo-4-chlorobutyrophenoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 136765185-Bromo-3-methyl-2,3-dihydro-1h-inden-1-oneYield 89.6%

Conditions

Temperature
180 °C

Procedure

To a mixture of sodium chloride (1.23 g, 21.0 mmol) and aluminum chloride (5.0 g, 38.2 mmol) at 130° C. was added 1-(4-bromophenyl)-4-chlorobutan-1-one (1.0 g, 3.82 mmol) and the resulting mixture was heated to 180° C. for 20 minutes. The mixture was allowed to cool to room temperature and quenched by portionwise addition to a cold 1N HCl solution (150 mL). The mixture was extracted several times with dichloromethane. The combined organic layers were separated, dried over magnesium sulfate, filtered, and concentrated to give 5-bromo-3-methyl-indan-1-one (0.77 g, 89%).

Workup

  1. temperatureto cool to room temperature
  2. customquenched by portionwise addition to a cold 1N HCl solution (150 mL)
  3. extractionThe mixture was extracted several times with dichloromethane
  4. customThe combined organic layers were separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cf9e36cb0904470097a4cc611ff816e5
Source dataset
uspto-grants-2008_08
Patent number
US07414142B2

Reaction notes

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