Bromine → 2-Bromo-5-fluoro-1-indanone

HRID 2247572Notes

Reaction equation

HRID 2247572 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7]2>C(O)(=O)C>[Br:1][CH:8]1[CH2:7][C:6]2[C:10](=[CH:11][CH:12]=[C:4]([F:3])[CH:5]=2)[C:9]1=[O:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 1365375-Fluoro-1-indanone

Product 1

HCID 110316412-Bromo-5-fluoro-1-indanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Bromine (1.98 mL) was added to a solution of 5-fluoroindanone (5.53 g) in acetic acid (100 mL), and the reaction solution was stirred at 60° C. for 10 minutes. After allowing the reaction solution to be cooled to room temperature, the solvent was evaporated under reduced pressure. Ethyl acetate and a saturated aqueous solution of sodium bicarbonate were added to the residue and the organic layer was partitioned. The resulting organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: heptane-ethyl acetate system) to obtain 8.43 g of the title compound. The physical properties of the compound are as follows.

Workup

  1. temperatureto be cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. additionEthyl acetate and a saturated aqueous solution of sodium bicarbonate were added to the residue
  4. customthe organic layer was partitioned
  5. dry with materialThe resulting organic layer was dried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-4485c197171c4ee5ad05cdd5ec21e388
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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