Bromotrimethylsilane → HCID 86641268, compound

HRID 386353Notes

Reaction equation

HRID 386353 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][P:9](=[O:16])([O:13]CC)[O:10]CC)(=[O:4])[CH:2]=[CH2:3].[CH3:17][Si:18](Br)([CH3:20])[CH3:19]>C(Cl)Cl>[C:1]([O:5][CH2:6][CH2:7][CH2:8][P:9](=[O:16])([O:13][Si:18]([CH3:20])([CH3:19])[CH3:17])[O:10][Si:18]([CH3:20])([CH3:19])[CH3:17])(=[O:4])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 866412693-(Diethoxyphosphinyl)propyl 2-propenoate

Product 1

HCID 86641268HCID 86641268, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of diethyl 3-acryloyloxypropylphosphonate (31.12 g; 0.124 moles) in CH2Cl2 (85 g) is added a solution of trimethylsilyl bromide (40 g; 0.261 moles) in CH2Cl2 (9.2 g) dropwise at room temperature. The mixture is refluxed for 4 hours. The solvent is evaporated on a rotary evaporator under reduced pressure to afford di(trimethylsilyl) 3-acryloyloxypropylphosphonate as a clear, colorless liquid (42.4 g; purity 95% by GC). 1H NMR (CDCl3, δ ppm) 0.006 (s, 9H, CH3—Si), 1.4-1.54 (m, 2H, CH2—P), 1.59-1.72 (m, 2H, CH2—CH2—), 3.91 (t, 2H, CH2—O), 5.55 (dd, 1H, CH═), 5.83 (dd, 1H, CH═), 6.12 (dd, 1H, CH═). 31P NMR (CDCl3, δ ppm) 13.55.

Workup

  1. temperatureThe mixture is refluxed for 4 hours
  2. customThe solvent is evaporated on a rotary evaporator under reduced pressure

Sources & evidence

ORD record
ord-8553b5a8a9c54441a796d045aec64ad6
Source dataset
uspto-grants-2013_02
Patent number
US08372516B2

Reaction notes

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