Chloroiodomethane → Di-tert-butyl (chloromethyl) phosphate

HRID 20210

Reaction equation

HRID 20210 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-13f9a7cc73b54c34b671626294596dc9
Source dataset
uspto-grants-2010_06
Patent number
US07745625B2

Linked notes

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