Hydrochloric Acid → 4-Bromo-7-fluoroindan-1-one

HRID 536472Notes

Reaction equation

HRID 536472 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[C:13](=[O:15])[CH2:12][CH2:11]2.[Br:16]Br.Cl>ClC(Cl)C>[Br:16][C:9]1[CH:8]=[CH:7][C:6]([F:5])=[C:14]2[C:10]=1[CH2:11][CH2:12][C:13]2=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24408BromineHCID 27827677-Fluoroindan-1-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 534401624-Bromo-7-fluoroindan-1-oneYield 64.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
65 °C

Procedure

To a room temperature solution of aluminum chloride (11.77 g, 88 mmol) in dichloroethane (100 mL) was added 7-fluoro-2,3-dihydro-1H-inden-1-one (5.3 g, 35.3 mmol) followed with bromine (1.91 mL, 37.1 mmol). The mixture was heated at 65° C. for 16 hours, then cooled to ambient temperature and poured into a mixture of ice and HCl (1N aqueous). The mixture was extracted twice with ether (200 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by chromatography (silica gel column eluting with 0-10% EtOAc/hexanes) to provide the title compound (5.2 g, 64%). MS (DCI/NH3) m/z 246 (M+NH4)+.

Workup

  1. temperaturecooled to ambient temperature
  2. extractionThe mixture was extracted twice with ether (200 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography (silica gel column eluting with 0-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cbf7ecc7154641d7ad6ef131b453762e
Source dataset
uspto-grants-2014_10
Patent number
US08859584B2

Reaction notes

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