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

HRID 1452109Notes

Reaction equation

HRID 1452109 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].CCOCC.[F:19][B-:20]([F:23])([F:22])[F:21].[H+].FF>C(#N)C>[F:19][B-:20]([F:23])([F:22])[F:21].[F:19][B-:20]([F:23])([F:22])[F:21].[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 8000Boron trifluoride etherateHCID 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 149.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,4-diazabicyclo[2.2.2]octane N-oxide (2.56 g, 20 mmole), boron trifluoride etherate (2.4 mL, 20 mmole), and tetrafluoroboric acid (50% solution, 3.66 g, 20 mmole) in acetonitrile (250 mL) was cooled to 8° C. and treated with a mixture of fluorine in nitrogen (10% V/V, 52 mmole). The reaction was evaporated, the remaining solid washed with acetone and dried to afford 4.8 grams of 1-hydroxyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (75% yield).

Workup

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

Sources & evidence

ORD record
ord-a3297480f1f649b088793bc3903d0c84
Source dataset
uspto-grants-1997_02
Patent number
US05606084

Reaction notes

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