4-Bromostyrene → Diphenylphosphinostyrene

HRID 729214Notes

Reaction equation

HRID 729214 reaction equation
[C:1]1([C:7]#[C:8]C#C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mg].BrC1C=CC(C=C)=CC=1.Cl[P:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH:7]([C:1]1[CH:2]=[CH:3][C:4]([P:22]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:5][CH:6]=1)=[CH2:8]

Participants

6

Reactant 4

HCID 162634-BromostyreneHCID 66180ChlorodiphenylphosphineHCID 5462224MagnesiumHCID 11355482Buta-1,3-diynylbenzene

Product 1

HCID 11437688Diphenylphosphinostyrene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Polymerizable Gold Complex (3-1) was synthesized by reacting the gold complex obtained by the reaction between sodium tetrachloroaurate (III) and triphenylphosphine having a polymerizable functional group, with phenylbutadiyne synthesized by a known method (see, P. Cadiot and W. Chodkiewicz, Chemistry of Acetylenes, H. G. Viehe, ed., Marcel Dekker, New York (1969)). More specifically, 20 ml of dried THF was added to 341 mg (14 mmol) of magnesium and thereto, a 10 ml THF solution containing 2.70 g (15 mmol) of 4-bromostyrene was added dropwise to prepare a Grignard reagent. To the resulting solution, a 10 ml THF solution containing 2.50 g (11 mmol) of chlorodiphenylphosphine was added dropwise and stirred at room temperature of 1.5 hours. After removing the solvent by distillation under reduced pressure, the residue was purified by silica gel column chromatography and recrystallized from a hexane solution to obtain 2.30 g (8.3 mmol) of (4-vinylphenyl)diphenylphosphine Compound (B).

Workup

  1. additionwas added dropwise
  2. additionwas added dropwise
  3. customAfter removing the solvent
  4. distillationby distillation under reduced pressure
  5. customthe residue was purified by silica gel column chromatography
  6. customrecrystallized from a hexane solution

Sources & evidence

ORD record
ord-223775f6a560431b879c384c695c6fee
Source dataset
uspto-grants-2009_09
Patent number
US07582363B2

Reaction notes

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