Boron trifluoride → 1-Benzoyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

HRID 1781119Notes

Reaction equation

HRID 1781119 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[C:6]([N+:14]12[CH2:21][CH2:20][N:17]([CH2:18][CH2:19]1)[CH2:16][CH2:15]2)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.B(F)(F)[F:23].FF>C(#N)C>[F:1][B-:2]([F:5])([F:4])[F:3].[F:1][B-:2]([F:5])([F:4])[F:3].[C:6]([N+:14]12[CH2:15][CH2:16][N+:17]([F:23])([CH2:18][CH2:19]1)[CH2:20][CH2:21]2)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 24524FluorineHCID 190480521-Benzoyl-4-aza-1-azoniabicyclo[2.2.2]octane tetrafluoroborate

Product 1

HCID 190480381-Benzoyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-benzoyl-4-aza-1-azoniabicyclo[2.2.2]octane tetrafiuoroborate (32 g, 10 mmole) and boron trifluoride gas (6.7 g, 10 mmole) in acetonitrile (125 mL) was cooled to 8° C. and treated with a mixture of fluorine in nitrogen (10 % V/V, 12 mmole). The reaction was evaporated, the remaining solid washed with DME and dried to afford 1-benzoyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate).

Workup

  1. customThe reaction was evaporated
  2. washthe remaining solid washed with DME
  3. customdried

Sources & evidence

ORD record
ord-6e157c5c567247129f5adc0a91e8d8c5
Source dataset
uspto-grants-1997_05
Patent number
US05631372

Reaction notes

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