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

HRID 451612

Reaction equation

HRID 451612 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-4b0788c3764f40829af90ba225641ad4
Source dataset
uspto-grants-2013_07
Patent number
US08487116B2

Linked notes

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