Water → 1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

HRID 1452110Notes

Reaction equation

HRID 1452110 reaction equation
[N:1]12[CH2:8][CH2:7][N+:4]([O-:9])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.O.[B:11]([F:14])([F:13])[F:12].[F:15]F>C(#N)C>[F:12][B-:11]([F:15])([F:14])[F:13].[F:12][B-:11]([F:15])([F:14])[F:13].[OH:9][N+:4]12[CH2:7][CH2:8][N+:1]([F:12])([CH2:6][CH2:5]1)[CH2:2][CH2:3]2

Participants

6

Reactant 4

HCID 962WaterHCID 6356Boron trifluorideHCID 24524FluorineHCID 111371811,4-Diazabicyclo(2.2.2)octane, 1-oxide

Product 1

HCID 27373291-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)Yield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,4-diazabicyclo[2.2.2]octane N-oxide (12.8 g, 0.1 mole), water (1.8 mL, 0.1 mole) and boron trifluoride (13.6 g, 0.2 mole) in acetonitrile (250 mL) was cooled to 8° C. and treated with a mixture of fluorine in nitrogen (10% V/V, 0.2 mole). The reaction was evaporated, the remaining solid washed with acetone and dried to afford 22 grams of 1-hydroxyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (68% yield).

Workup

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

Sources & evidence

ORD record
ord-03d24502c2ed469781e6b188e2cfb98f
Source dataset
uspto-grants-1997_02
Patent number
US05606084

Reaction notes

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