Phosphorodichloridous acid, methyl ester → Di[p-(3-phenylpropyl)phenyl]chlorophosphine

HRID 1638231Notes

Reaction equation

HRID 1638231 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Li])=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[P:19]([Cl:21])Cl>>[C:1]1([CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([P:19]([C:13]3[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:11][CH:12]=3)[Cl:21])=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 76768Phosphorodichloridous acid, methyl esterHCID 178506705HCID 178506705, compound

Product 1

HCID 11113246Di[p-(3-phenylpropyl)phenyl]chlorophosphineYield 90%

Procedure

p-(3-phenylpropyl)phenyllithium (8.1 g, 40 mmol) in 150 ml solvent (Et2O/THF 1/1) was added dropwise to CH3OPCl2 (2.66 g, 20 mmol) in 70 ml solvent (Et2O/THF 1/1) at -70° C. The addition was completed in 2 h. The reaction mixture was stirred overnight at room temperature and then brought to reflux for 2 h. The precipitate was filtered and the solvent of the solution was removed by applying vacuum. PCl3 (15 ml) was added to the resulting viscous oil and stirred for 24 h. Then the mixture was kept at 70° C. and 1 mm Hg for 2 h to remove excess PCl3 and byproduct. The product, di[p-(3-phenylpropyl)phenyl]chlorophosphine, was obtained as a pale yellow viscous oil with 90% yield. The product was characterized by 31P NMR. 83.6.

Workup

  1. additionThe addition
  2. temperatureto reflux for 2 h
  3. filtrationThe precipitate was filtered
  4. customthe solvent of the solution was removed
  5. additionPCl3 (15 ml) was added to the resulting viscous oil
  6. stirringstirred for 24 h
  7. customwas kept at 70° C.
  8. custom1 mm Hg for 2 h to remove excess PCl3 and byproduct

Sources & evidence

ORD record
ord-aaa8940c102d42d5aab1b8a641876eef
Source dataset
uspto-grants-2000_03
Patent number
US06043398

Reaction notes

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