N-bromobutanimide → 3-Bromo-6-fluoro-1-indanone

HRID 362863Notes

Reaction equation

HRID 362863 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:18]=[C:17]2[C:13]([CH2:14][CH2:15][C:16]2=[O:19])=[CH:12][CH:11]=1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][CH:14]1[C:13]2[C:17](=[CH:18][C:10]([F:9])=[CH:11][CH:12]=2)[C:16](=[O:19])[CH2:15]1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 15194646-Fluoro-1-indanone

Product 1

HCID 232936813-Bromo-6-fluoro-1-indanoneYield 66%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of N-bromosuccinimide (2.76 g, 15.51 mmoles, Aldrich), benzoyl peroxide (0.01 g, 0.04 mmoles, Aldrich) and 6fluoro-1-indanone (2.29 g, 15.25 mmoles) in carbon tetrachloride (20 mL) was refluxed under nitrogen for two hours. The mixture was cooled to ambient temperature, filtered, and the solids were washed with dichloromethane. The washings and filtrate were combined, washed successively with 1.0N sodium hydroxide (2×30 mL), water (2×30 mL) and brine (30 mL), and evaporated in vacuo. The residue was chromatographed on silica gel eluting first with hexane, gradually increasing the polarity to hexane: ethyl acetate (95:5). The fractions containing the major spot were combined and evaporated in vacuo to give a 2.30 g (66%) of 3-bromo-6-fluoro-1-indanone as a yellow oil which was used without further purification.

Workup

  1. temperaturewas refluxed under nitrogen for two hours
  2. filtrationfiltered
  3. washthe solids were washed with dichloromethane
  4. washwashed successively with 1.0N sodium hydroxide (2×30 mL), water (2×30 mL) and brine (30 mL)
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel eluting first with hexane
  7. temperaturegradually increasing the polarity to hexane: ethyl acetate (95:5)
  8. additionThe fractions containing the major spot
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-8a039992bf8242619c960b12b726dc7b
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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