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

HRID 2210643Notes

Reaction equation

HRID 2210643 reaction equation
[N:1]12[CH2:8][CH2:7][N+:4]([O-:9])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.B(F)(F)[F:11].[F:14][B-:15]([F:18])([F:17])[F:16].[H+].FF>O>[F:14][B-:15]([F:18])([F:17])[F:16].[F:14][B-:15]([F:18])([F:17])[F:16].[OH:9][N+:4]12[CH2:7][CH2:8][N+:1]([F:11])([CH2:6][CH2:5]1)[CH2:2][CH2:3]2

Participants

6

Reactant 4

HCID 6356Boron trifluorideHCID 24524FluorineHCID 28118Tetrafluoroboric acidHCID 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 159.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1,4-diazabicyclo[2.2.2]octane N-oxide (25.6 g, 0.2 mole), boron trifluoride gas (13.6 g, 0.2 mole), and tetrafluoroboric acid (10 M solution, 20 mL, 0.2 mole) in water (400 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 51.4 grams of 1-hydroxyl-4-fluoro-1,4-diazoniabicyclo [2.2.2]octane bis(tetrafluoroborate) (80% yield).

Workup

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

Sources & evidence

ORD record
ord-49b27572016f47f99615c2b861a9e223
Source dataset
uspto-grants-1995_10
Patent number
US05459267

Reaction notes

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