Tetrahydrofuran → 4-(Divinyl-phosphinoyl)nitro benzene

HRID 472667Notes

Reaction equation

HRID 472667 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([P:10](Cl)(Cl)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:14]([Mg]Br)=[CH2:15].O1CC[CH2:20][CH2:19]1>>[CH:19]([P:10]([CH:14]=[CH2:15])([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:11])=[CH2:20]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 13486298(4-Nitrophenyl)phosphonic dichlorideHCID 178418507HCID 178418507, compound

Product 1

HCID 580713594-(Divinyl-phosphinoyl)nitro benzene

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-Nitrophenylphosphonic dichloride (2.14 g, 8.91 mmol) in tetrahydrofuran at −78° C. was added vinylmagnesium bromide (2.34 g, 17.8 mmol). The solution was stirred at −78° C. for one hour then quenched by the addition of ammonium chloride solution. The mixture was extracted with dichloromethane. The combined organic layers were dried and concentrated. 4-(Divinyl-phosphinoyl)nitro benzene was isolated as a brown-yellow oil (1.69 g, 85%). MS=224 (MH)+.

Workup

  1. customthen quenched by the addition of ammonium chloride solution
  2. extractionThe mixture was extracted with dichloromethane
  3. customThe combined organic layers were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-450c10ee75484b8b975f9ded2b1d043b
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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