Bromotrimethylsilane → HCID 86750672, compound

HRID 53107Notes

Reaction equation

HRID 53107 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([P:20]([O:25]CC)(=[O:24])[O:21]CC)[P:12]([O:17]CC)(=[S:16])[O:13]CC.C[Si](Br)(C)C>C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([P:20]([OH:24])(=[O:21])[OH:25])[P:12]([OH:13])(=[S:16])[OH:17]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86750673HCID 86750673, compound

Product 1

HCID 86750672HCID 86750672, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, to a solution of 8.04 g (18 mmol) of tetraethyl 2-naphthylthiomethane-diphosphonate obtained in Example 1 in dry methylene chloride (100 ml) was added dropwise 27.56 g (180 mmol) of trimethylsilyl bromide at room temperature and then the mixture was stirred at room temperature for 72 hours. After the solvent and the excess trimethylsilyl bromide were distilled off under reduced pressure, the resulting residue was dissolved in a mixed solvent of water:methanol=5:95, and the solution was heated to reflux for 30 minutes, and the solvent was again distilled off under reduced pressure. The resulting residue was crystallized from acetone/methylene chloride and the obtained crystals were recrystallized from the same solvent to obtain the title compound as white crystals. The yield was 86%.

Workup

  1. distillationAfter the solvent and the excess trimethylsilyl bromide were distilled off under reduced pressure
  2. dissolutionthe resulting residue was dissolved in a mixed solvent of water
  3. temperaturemethanol=5:95, and the solution was heated
  4. temperatureto reflux for 30 minutes
  5. distillationthe solvent was again distilled off under reduced pressure
  6. customThe resulting residue was crystallized from acetone/methylene chloride
  7. customthe obtained crystals were recrystallized from the same solvent

Sources & evidence

ORD record
ord-9d10cb0defc942958442a1b357dab284
Source dataset
uspto-grants-1997_04
Patent number
US05618804

Reaction notes

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