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Tributylamine → Difluoromethylene diphosphonate

HRID 1181909
Notes
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Reaction equation

HRID 1181909 reaction equation
[F:1][C:2]([F:23])([P:13](=[O:22])([O:18]C(C)C)[O:14]C(C)C)[P:3](=[O:12])([O:8]C(C)C)[O:4]C(C)C.C[Si](Br)(C)C.C(N(CCCC)CCCC)CCC>C(#N)C.CN(C=O)C>[F:23][C:2]([F:1])([P:3](=[O:4])([OH:12])[OH:8])[P:13](=[O:14])([OH:18])[OH:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7622TributylamineHCID 76113BromotrimethylsilaneHCID 11717839tetraisopropyl difluoromethylenediphosphonate

Product 1

HCID 73182Difluoromethylene diphosphonateYield 300.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
41 °C

Procedure

To a stirred solution of tetraisopropyl difluoromethylenediphosphonate (2.0 g, 5.26 mmol) in anhydrous acetonitrile (30 mL) was added dropwise trimethylsilyl bromide (4.17 mL, 31.58 mmol). The resulting solution was stirred at 40-42° C. for 24 h, concentrated to dryness, and coevaporated with anhydrous acetonitrile once. The residue was re-dissolved in an acetonitrile/water mixture, and then coevaporated with DMF. The residue was dissolved in a DMF solution of tributylamine (1.93 g, 2.48 mL, 10.43 mmol), transferred into multiple small flasks, concentrated to dryness, and coevaporated with anhydrous DMF three times. The residue was dried in a vacuum oven at 40° C. for 4 h to give a slightly yellow residue (3.35 g).

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was re-dissolved in an acetonitrile/water mixture
  3. customtransferred into multiple small flasks
  4. concentrationconcentrated to dryness
  5. customThe residue was dried in a vacuum oven at 40° C. for 4 h

Sources & evidence

ORD record
ord-7fa1df5cd85944779df427feb22463b3
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07285658B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes