Bromotrimethylsilane → HCID 21953562, compound

HRID 2304133Notes

Reaction equation

HRID 2304133 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][CH:11]([CH3:28])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:27])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:26])[CH2:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])([O:6]CC)=[O:5])C.Br[Si](C)(C)C>ClCCl>[P:4]([CH2:9][CH2:10][CH:11]([CH3:28])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:27])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:26])[CH2:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])([OH:6])([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 18462421HCID 18462421, compound

Product 1

HCID 21953562HCID 21953562, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 14.6 g (35 mmol) of 1-(diethylphosphono)-3,7,11,15-tetramethylhexadecane in 40 mL of dichloromethane was added 15.0 g (98 mmol) of bromotrimethylsilane. After 24 h at room temperature, the solution was concentrated to a pale yellowish liquid, and the intermediate silylphosphonate ester was dissolved in 100 mL of methanol. The resultant solution was stirred at room temperature for 30 min and concentrated to a white solid. Dissolution in methanol and concentration were repeated two times, and recrystallization from ethyl acetate afforded 10.5 g (83%) of 1-phosphono-3,7,11,15-tetramethylhexadecane as white crystals, mp 69-72° C.

Workup

  1. concentrationthe solution was concentrated to a pale yellowish liquid
  2. dissolutionthe intermediate silylphosphonate ester was dissolved in 100 mL of methanol
  3. concentrationconcentrated to a white solid
  4. dissolutionDissolution in methanol
  5. concentrationconcentration
  6. customtwo times, and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-fe31d0016f0d4e1e85a63e72acff7df5
Source dataset
uspto-grants-2002_08
Patent number
US06433359B1

Reaction notes

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