Chloroiodomethane → Di-tert-butyl (chloromethyl) phosphate

HRID 539845Notes

Reaction equation

HRID 539845 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-a3c0da4214e14c42b37e1fd0b74820b2
Source dataset
uspto-grants-2014_10
Patent number
US08871771B2

Reaction notes

Loading…