Sodium Bicarbonate → Di-tert-butyl (chloromethyl) phosphate

HRID 882349

Reaction equation

HRID 882349 reaction equation
[C:1]([O:5][P:6]([O-:13])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[K+].C(=O)(O)[O-].[Na+].S(Cl)(O[CH2:24][Cl:25])(=O)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.C(Cl)Cl>[P:6]([O:13][CH2:24][Cl:25])([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 2733556Chloromethyl chlorosulfateHCID 23674467Potassium di-tert-butyl phosphate

Product 1

HCID 11701630Di-tert-butyl (chloromethyl) phosphateYield 59.3%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of potassium di-tert-butylphosphate (2.45 g, 9.51 mmol), sodium bicarbonate (3.19 g, 38.0 mmol) and tetrabutylammonium hydrogen sulfate (340.2 mg, 0.972 mmol) in water (80 mL), was added methylene chloride (50 mL). The mixture was cooled to 0° C. and stirred vigorously under argon for 10 min. Chloromethyl chlorosulfate (1.92 g, 1.2 mL, 11.6 mmol) in methylene chloride (30 mL) was added slowly and the reaction was stirred at room temperature overnight. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate and concentrated to give di-tert-butyl chloromethyl phosphate as a colorless oil (1.46 g, 59% yield).

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3119adfdbd844883a243af3c9a9828b8
Source dataset
uspto-grants-2015_03
Patent number
US08993614B2

Linked notes

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