Chloroiodomethane → Di-tert-butyl (chloromethyl) phosphate

HRID 1256950Notes

Reaction equation

HRID 1256950 reaction equation
[C:1]([O:5][P:6]([O-:13])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:31][CH2:32]I>>[P:6]([O:13][CH2:32][Cl:31])([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

3

Reactant 2

HCID 11644ChloroiodomethaneHCID 22339116Tetra-n-butylammonium di-tert-butylphosphate

Product 1

HCID 11701630Di-tert-butyl (chloromethyl) phosphate

Procedure

A mixture of tetrabutylammonium di-tert-butyl phosphate (57 g, 0.126 mol, Digital Specialty Chemicals) and chloroiodomethane (221 g, 1.26 mol) was stirred at room temperature for four hours before the volatiles were removed under vacuum. 500 ml of ethyl ether was added to the residue and insoluble solid was filtered away. Concentration of the filtrate in vacuo and removal of remaining volatiles using a vacuum pump provided di-tert-butyl chloromethyl phosphate as a light brown or yellow oil, which was utilized in the next step without further purification.

Workup

  1. customwere removed under vacuum
  2. addition500 ml of ethyl ether was added to the residue and insoluble solid
  3. filtrationwas filtered away
  4. customConcentration of the filtrate in vacuo and removal of remaining volatiles

Sources & evidence

ORD record
ord-f52f1c7d63574a26a58b2e7a3f705772
Source dataset
uspto-grants-2013_06
Patent number
US08461333B2

Reaction notes

Loading…