Bromotrimethylsilane → HCID 86641270, compound

HRID 386355Notes

Reaction equation

HRID 386355 reaction equation
[C:1]([O:6][CH2:7][CH2:8][CH2:9][P:10](=[O:17])([O:14]CC)[O:11]CC)(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH3:18][Si:19](Br)([CH3:21])[CH3:20]>C(Cl)Cl>[C:1]([O:6][CH2:7][CH2:8][CH2:9][P:10](=[O:17])([O:14][Si:19]([CH3:21])([CH3:20])[CH3:18])[O:11][Si:19]([CH3:21])([CH3:20])[CH3:18])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86641271HCID 86641271, compound

Product 1

HCID 86641270HCID 86641270, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of diethyl 3-methacryloyloxypropylphosphonate (28.2 g; 0.107 moles) in CH2Cl2 (60 g) is added dropwise a solution of trimethylsilyl bromide (34.4 g; 0.225 moles) in CH2Cl2 (22 g) at room temperature. The mixture is refluxed for 5 hours. The solvent is evaporated under vacuum to give di(trimethylsilyl) 3-methacryloyloxypropylphosphonate as a clear, colorless liquid (37.9 g). 1H NMR (CDCl3, δ ppm) 0.01 (s, 9H, CH3—Si), 1.41-1.55 (m, 2H, CH2—P), 1.59-1.73 (m, 2H, CH2—CH2—P), 1.66 (d, 3H, CH3), 3.90 (t, 2H, CH2—O), 5.28 (s, 1H, CH═), 5.82 (s, 1H, CH═). 31P NMR (CDCl3, δ ppm) 13.6.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. customThe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-3662da2b15fd4528b32394a2251521ca
Source dataset
uspto-grants-2013_02
Patent number
US08372516B2

Reaction notes

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