Bromotrimethylsilane → HCID 22630518, compound

HRID 2416969Notes

Reaction equation

HRID 2416969 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([F:25])([F:24])[C:14]([F:23])([F:22])[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])([O:6]CC)=[O:5])C.Br[Si](C)(C)C>ClCCl.CO>[P:4]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([F:24])([F:25])[C:14]([F:22])([F:23])[C:15]([F:20])([F:21])[C:16]([F:17])([F:18])[F:19])([OH:5])([OH:6])=[O:3]

Participants

5

Reactant 2

HCID 76113BromotrimethylsilaneHCID 22630503HCID 22630503, compound

Product 1

HCID 22630518HCID 22630518, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 11.54 g of 1-(diethylphosphono)-4-(nonafluorobutyl)butane in 50 mL of dichloromethane was added 10.7 g of bromotrimethylsilane. After 18 hr at room temperature, the solution was concentrated to a nearly colorless liquid, and the intermediate silylphosphonate ester was dissolved in 250 mL of methanol. The resultant solution was stirred at room temperature for 1 hr, and then concentrated to give a white solid. Dissolution in methanol and concentration were repeated two more times, and recrystallization of the crude product from acetonitrile gave 8.39 g of 1-phosphono-4-(nonafluorobutyl)butane (CF3(CF2)3(CH2)4PO3H2) as colorless needles, m.p. 123-124° C.

Workup

  1. concentrationthe solution was concentrated to a nearly colorless liquid
  2. dissolutionthe intermediate silylphosphonate ester was dissolved in 250 mL of methanol
  3. concentrationconcentrated
  4. customto give a white solid
  5. concentrationconcentration
  6. customtwo more times, and recrystallization of the crude product from acetonitrile

Sources & evidence

ORD record
ord-448aad817a8e4b7d8b45243c16820de4
Source dataset
uspto-grants-2004_11
Patent number
US06824882B2

Reaction notes

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