Bromotrimethylsilane → HCID 22630500, compound

HRID 2416983Notes

Reaction equation

HRID 2416983 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([F:43])([F:42])[C:32]([F:41])([F:40])[C:33]([F:39])([F:38])[C:34]([F:37])([F:36])[F:35])([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][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([F:42])([F:43])[C:32]([F:40])([F:41])[C:33]([F:38])([F:39])[C:34]([F:35])([F:36])[F:37])([OH:6])([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 22630521HCID 22630521, compound

Product 1

HCID 22630500HCID 22630500, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.05 g of 1-(diethylphosphono)-22-(nonafluorobutyl)docosane in 10 mL of dichloromethane was added 0.61 g of bromotrimethylsilane. After 18 hr at room temperature, the solution was concentrated to a beige grease to which was added 30 mL of methanol. A white solid formed, and the resultant mixture was stirred at room temperature for 30 min. Removal of the solvent under reduced pressure left a white solid, which was slurried with an additional 20 mL of methanol for 30 min. Removal of solvent again left a white solid, and recrystallization of the crude product from methanol provided 0.61 g of 1-phosphono-22-(nonafluorobutyl)docosane (CF3(CF2)3(CH2)22PO3H2) as white crystals, m.p. 106-108° C.

Workup

  1. concentrationthe solution was concentrated to a beige grease to which
  2. additionwas added 30 mL of methanol
  3. customA white solid formed
  4. customRemoval of the solvent under reduced pressure
  5. waitleft a white solid, which
  6. waitwas slurried with an additional 20 mL of methanol for 30 min
  7. customRemoval of solvent
  8. waitagain left
  9. customa white solid, and recrystallization of the crude product from methanol

Sources & evidence

ORD record
ord-1b23fcc727ce4373a2b66d13a453f902
Source dataset
uspto-grants-2004_11
Patent number
US06824882B2

Reaction notes

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