Chloroiodomethane → Di-tert-butyl (chloromethyl) phosphate

HRID 1256949Notes

Reaction equation

HRID 1256949 reaction equation
[P:1]([O-:13])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cl:14][CH2:15]I>>[P:1]([O:13][CH2:15][Cl:14])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:2]

Participants

3

Reactant 2

HCID 11644ChloroiodomethaneHCID 4191557Ditert-butyl phosphate

Product 1

HCID 11701630Di-tert-butyl (chloromethyl) phosphateYield 343.6%

Procedure

The tetrabutylammonium salt of bis-tert butyl phosphate (57 g, 0.126 mol, Digital Specialty Chemicals) and chloroiodomethane (221 g, 1.26 mol) were stirred at room temperature for four hours and then the volatiles were removed in vacuo. 500 ml of ethyl ether was added to the residue and insoluble solid was filtered away. Concentration of the filtrate and final removal of volatiles using a vacuum pump provided di-tert-butyl chloromethyl phosphate (112 g), typically as a light yellow or brown oil, which was utilized in the next step without any further purification.

Workup

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

Sources & evidence

ORD record
ord-6d5b7b536aa54e55872b9ec36fb39d1b
Source dataset
uspto-grants-2013_06
Patent number
US08461333B2

Reaction notes

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