Bromotrimethylsilane → HCID 22630513, compound

HRID 2416973Notes

Reaction equation

HRID 2416973 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([F:29])([F:28])[C:18]([F:27])([F:26])[C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])([O:6]CC)=[O:5])C.Br[Si](C)(C)C>ClCCl>[P:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([F:28])([F:29])[C:18]([F:26])([F:27])[C:19]([F:24])([F:25])[C:20]([F:21])([F:22])[F:23])([OH:5])([OH:6])=[O:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 22630506HCID 22630506, compound

Product 1

HCID 22630513HCID 22630513, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.03 g of 1-(diethylphosphono)-8-(nonafluorobutyl)octane in 30 mL of dichloromethane was added 6.12 g of bromotrimethylsilane. After 18 hr at room temperature, the solution was concentrated to a pale yellow liquid, and the intermediate silylphosphonate ester was dissolved in 150 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 two recrystallizations of the crude product from acetonitrile gave 4.68 g of 1-phosphono-8-(nonafluorobutyl)octane (CF3(CF2)3(CH2)8PO3H2) as white crystals, m.p. 87-89° C.

Workup

  1. concentrationthe solution was concentrated to a pale yellow liquid
  2. dissolutionthe intermediate silylphosphonate ester was dissolved in 150 mL of methanol
  3. concentrationconcentrated to a white solid
  4. dissolutionDissolution in methanol
  5. concentrationconcentration
  6. customtwo times, and two recrystallizations of the crude product from acetonitrile

Sources & evidence

ORD record
ord-89b84894020b4497a20051ff572a3832
Source dataset
uspto-grants-2004_11
Patent number
US06824882B2

Reaction notes

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