Water → Di-tert-butyl (chloromethyl) phosphate

HRID 1429718Notes

Reaction equation

HRID 1429718 reaction equation
[C:1]([O:5][P:6](=[O:13])([OH:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].O.[CH2:20](Cl)[Cl:21]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:21][CH2:20][O:13][P:6](=[O:12])([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6344Dichloromethane2×HCID 429756Phosphoric acid, bis(1,1-dimethylethyl) esterHCID 516892Sodium Bicarbonate

Product 1

HCID 11701630Di-tert-butyl (chloromethyl) phosphateYield 64%

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Conditions

Temperature
0 °C

Procedure

A mixture of Phosphoric acid di-tert-butyl ester (1 g, 0.0048 mol), NaHCO3 (0.806 g, 0.0096 mol), tetra butyl ammonium hydrogen sulphate (0.163 g, 0.00048 mol), water (40 ml) and DCM (25 ml) were taken. The mixture was cooled to 0° C. and stirred at that temperature for 20 minutes. Chloromethyl chlorosulphatc, (0.943 g, 0.0057 mol) in DCM (15 ml) was added to it at 0° C. The reaction mixture allowed to warm to room temperature and stirred for 18 hours. The organic layer was separated and aqueous layer was extracted with DCM (30 ml). The organic layer was washed with brine (60 ml) solution and dried over Na2SO4. The organic layer was evaporated to obtain Phosphoric acid di-tert-butyl ester chloromethyl ester as colorless oil (0.79 g, 64%).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 18 hours
  3. customThe organic layer was separated
  4. extractionaqueous layer was extracted with DCM (30 ml)
  5. washThe organic layer was washed with brine (60 ml) solution
  6. dry with materialdried over Na2SO4
  7. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-050a6aa85cc04bbba28b851396e56632
Source dataset
uspto-grants-2015_01
Patent number
US08940751B2

Reaction notes

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