Chloroiodomethane → Di-tert-butyl (chloromethyl) phosphate

HRID 1919290Notes

Reaction equation

HRID 1919290 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-f5b56fa72c524b4dad2f4cfc38d09b66
Source dataset
uspto-grants-2012_05
Patent number
US08168615B2

Reaction notes

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