Ammonium Chloride → Benzyl-di-t-butylphosphine

HRID 1394386Notes

Reaction equation

HRID 1394386 reaction equation
[C:1]([P:5]([C:7]([CH3:10])([CH3:9])[CH3:8])Cl)([CH3:4])([CH3:3])[CH3:2].[CH2:11]([Mg]Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>C1COCC1>[CH2:11]([P:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:1]([CH3:4])([CH3:3])[CH3:2])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 139566Di-tert-butylchlorophosphineHCID 178418336HCID 178418336, compound

Product 1

HCID 11170394Benzyl-di-t-butylphosphine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Di-t-butylchlorophosphine (75.0 g (0.415 mole)) and 0.5 mole of 12M solution of benzylmagnesium chloride in THF (200 ml) were refluxed under argon for 2 days. The reaction mixture was allowed to cool off to RT and an aqueous solution of ammonium chloride was added slowly. The organic phase was separated, and dried with magnesium sulfate. After removal of the solvent, the product was purified by distillation in vacuum. The yield of benzyldi-t-butylphosphine was 94.3 g (96%) with b.p. 56-59° C./0.1 mm. 31-P-NMR (CDCl3)+36.63 ppm. 1H NMR (CDCl3) 1.18 (s, 9H, Me3C), 1.20 (s, 9H, Me3C), 2.90 (d, 2JPH=2.92 Hz, P—CH2-Ph), 7.1-7.6 (m, 5H, aromatic protons).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried with magnesium sulfate
  3. customAfter removal of the solvent
  4. distillationthe product was purified by distillation in vacuum

Sources & evidence

ORD record
ord-29716fda34dd4dce8d905341414c82a0
Source dataset
uspto-grants-2008_03
Patent number
US07348388B2

Reaction notes

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