1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) → 5-Tert-butyl-2-fluoro-indan-1-one

HRID 2223405Notes

Reaction equation

HRID 2223405 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)[F:16].[B-](F)(F)(F)F.C1[N+]2(O)CC[N+](F)(CC2)C1>CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[CH:9]([F:16])[CH2:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 27373291-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)HCID 110305765-Tert-butyl-2,3-dihydroinden-1-one

Product 1

HCID 671882305-Tert-butyl-2-fluoro-indan-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-tert-butyl-indan-1-one (7.53 g, 40 mmol) was dissolved in methanol (400 ml). Accufluor (32.18 g) was added, and the reaction heated to reflux for 2 hours. After cooling and removing the solvent under vacuum, the residue was taken in methylene chloride and filtered. The filtrate was washed with water, dried with magnesium sulfate, and filtered, and the solvent removed under vacuum to give 5-tert-Butyl-2-fluoro-indan-1-one, which was used without further purification. 1H NMR (300 MHz, CDCl3) 7.73 (d, 1H), 7.48 (d, 1H), 7.45 (s, 1H), 5.18-5.35 (m, 1H), 3.54-3.65 (m, 1H), 3.12-3.29 (m, 1H), 1.36 (s, 9H). MS (CSI) m/e 224 (M+NH4)+

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter cooling
  4. customremoving the solvent under vacuum
  5. filtrationfiltered
  6. washThe filtrate was washed with water
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-3860a5dcdef74d57901f5ed60da94572
Source dataset
uspto-grants-2008_05
Patent number
US07375126B2

Reaction notes

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