Ammonium Chloride → Benzyl-di-t-butylphosphine

HRID 910571Notes

Reaction equation

HRID 910571 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 benzyl-di-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-a042a629317b40d59d55cbe9c9e50021
Source dataset
uspto-grants-2011_09
Patent number
US08022152B2

Reaction notes

Loading…