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Phenyl phosphorus dichloride → DI-Tert-butylphenylphosphonium tetrafluoroborate

HRID 2261724
Notes
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Reaction equation

HRID 2261724 reaction equation
[Br-].[Li+].Cl[P:4](Cl)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:12]([Mg]Cl)([CH3:15])([CH3:14])[CH3:13].[H+].[B-:19]([F:23])([F:22])([F:21])[F:20]>CCOCC.CCCCCC>[F:20][B-:19]([F:23])([F:22])[F:21].[C:12]([PH+:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([CH3:15])([CH3:14])[CH3:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 12573Phenyl phosphorus dichlorideHCID 28118Tetrafluoroboric acid2×HCID 82050Lithium BromideHCID 178418310HCID 178418310, compound

Product 1

HCID 11220595DI-Tert-butylphenylphosphonium tetrafluoroborate

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 8058HexaneSolvent2×

Conditions

Temperature
0 °C

Procedure

In a round-bottomed flask, 60.6 mg of copper(I) bromide-dimethyl sulphide complex and 51.2 mg of lithium bromide are initially charged under protective gas. 20 ml of hexane, 4 ml of dichlorophenylphosphine and another 19 ml of hexane are subsequently added. The reaction solution is cooled to 0° C. 32.4 ml of a 2 M solution of tert-butylmagnesium chloride in ether are then slowly added dropwise. The mixture is subsequently allowed to slowly adjust to room temperature and is then stirred at room temperature for a further two hours. For workup, the mixture is cautiously admixed with 75 ml of degassed 2 M HBF4. Another 5 ml of 8 M HBF4 are then additionally added and stirred for 15 min. Filtration with suction is then effected and the filter cake is washed with a little cold water. The residue is dried under reduced pressure to constant weight. Yield: 7.9 g (86% of theory) purity >99%.

Workup

  1. customto slowly adjust to room temperature
  2. stirringstirred for 15 min
  3. filtrationFiltration with suction
  4. washthe filter cake is washed with a little cold water
  5. customThe residue is dried under reduced pressure to constant weight

Sources & evidence

ORD record
ord-e89df2b5f1c3483bbef092f5942427d3
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07847126B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes