Chloroiodomethane → Di-tert-butyl (chloromethyl) phosphate

HRID 539843Notes

Reaction equation

HRID 539843 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>C1C=CC=CC=1>[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

4

Reactant 2

HCID 11644ChloroiodomethaneHCID 4191557Ditert-butyl phosphate

Product 1

HCID 11701630Di-tert-butyl (chloromethyl) phosphate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The tetrabutylammonium salt of bis-tert butyl phosphate (45.1 g, 0.1 mol) and chloroiodomethane (200 g, 1.14 mol) were combined in 100 ml of benzene and the mixture was stirred at room temperature for four hours and then the benzene was removed under vacuum. A portion of 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 the volitiles on a vacuum pump provided di-tert-butyl chloromethyl phosphate, as a light yellow or light brown oil which was utilized in the next step without further purification.

Workup

  1. customthe benzene was removed under vacuum
  2. additionA portion of 500 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 the volitiles on a vacuum pump

Sources & evidence

ORD record
ord-5f0cc741e0c34e4c9ac7ccf943559caf
Source dataset
uspto-grants-2014_10
Patent number
US08871771B2

Reaction notes

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