Bromotrimethylsilane → HCID 19033968, compound

HRID 265238Notes

Reaction equation

HRID 265238 reaction equation
[C:1]([C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([P:30](=[O:37])([O:34]CC)[O:31]CC)[P:22](=[O:29])([O:26]CC)[O:23]CC)[CH:17]=[CH:18][CH:19]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C[Si](Br)(C)C>C(Cl)Cl.O1CCCC1.O>[C:1]([C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([P:30](=[O:31])([OH:34])[OH:37])[P:22](=[O:23])([OH:26])[OH:29])[CH:17]=[CH:18][CH:19]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 76113BromotrimethylsilaneHCID 53857274HCID 53857274, compound

Product 1

HCID 19033968HCID 19033968, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Tetraethyl [2-[3-(1-tridecynyl)phenyl]ethenylidene]bisphosphonate (3,247 g, 5.85 mmol) prepared according to Example 1 was dissolved in a mixture of CH2Cl2 --CD2Cl2 (25 ml, 4:1), and stirred under argon while trimethylsilyl bromide (3.5 ml, 26.5 mmol) was added. After the reaction was stirred for 6.5 hours, the solvent was removed under reduced pressure and the residue was briefly placed on the vacuum line. Hydrolysis was effected in tetrahydrofuran-water (9:1, 10 ml), stirring for 39 hours at room temperature. After stripping off the solvent, the residue was recrystallized from heptane-ether to give the product as a white solid, 0.416 g, 0.94 mmol, 16% yield; 1H NMR (CD3OD) ∂0.89 (t, J=6.9 Hz, 3H), 1.21 to 1.65 (several m, 18H), 2.40 (t, J=7.0 Hz, 2H), 7.55 (m, 2H), 7.71 (m, 2H), 8.03 (dd, J=46.1, 29.2 Hz, 1H); HRMS calcd for (M+H)+C21H33O6P2 m/z 443.1752, found 443.1700.

Workup

  1. additionwas added
  2. customthe solvent was removed under reduced pressure
  3. customHydrolysis
  4. stirringstirring for 39 hours at room temperature
  5. customthe residue was recrystallized from heptane-ether

Sources & evidence

ORD record
ord-e3d706c29d8f498cbecfd30ea1cdacfa
Source dataset
uspto-grants-1997_07
Patent number
US05648349

Reaction notes

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