Bromotrimethylsilane → HCID 22630495, compound

HRID 2416966Notes

Reaction equation

HRID 2416966 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([F:27])([F:26])[C:16]([F:25])([F:24])[C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])([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][C:15]([F:26])([F:27])[C:16]([F:24])([F:25])[C:17]([F:22])([F:23])[C:18]([F:19])([F:20])[F:21])([OH:5])([OH:6])=[O:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 22630516HCID 22630516, compound

Product 1

HCID 22630495HCID 22630495, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 18.63 g of 1-(diethylphosphono)-6-(nonafluorobutyl)hexane in 100 mL of dichloromethane was added 16.8 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 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 a 99:1 mixture of heptane and 2-propanol gave 12.50 g of 1-phosphono-6-(nonafluorobutyl)hexane (CF3(CF2)3(CH2)6PO3H2) as colorless leaves, m.p. 107-108° 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 to a white solid
  4. dissolutionDissolution in methanol
  5. concentrationconcentration
  6. customtwo times, and two recrystallizations of the crude product
  7. additionfrom a 99:1 mixture of heptane and 2-propanol

Sources & evidence

ORD record
ord-65f72e8edfce4ad0820a8de364a8c172
Source dataset
uspto-grants-2004_11
Patent number
US06824882B2

Reaction notes

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