Triphenylphosphine → Triphenylphosphane dibromide

HRID 917922Notes

Reaction equation

HRID 917922 reaction equation
[Br:1]C(C)(CBr)C(OC(N(F)F)CN(F)F)=O.[C:17]1([P:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(OCC)C>[Br-:1].[Br-:1].[C:30]1([P:23]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 21524290HCID 21524290, compound

Product 1

HCID 12890784Triphenylphosphane dibromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Employing a system similar to that used in Example I, 20.8 parts (0.055 mole) 1,2-bis(difluoramino)ethyl α,β-dibromoisobutyrate is added over a period of thirty minutes to 14.45 parts (0.055 mole) triphenylphosphine in 200 ml. of anhydrous diethyl ether to give an immediate precipitate of triphenylphosphine dibromide. Another 100 ml. of anhydrous ether is added during the course of the addition to facilitate stirring of the mixture. After 18 hours the mixture is filtered free of solids followed by removal of the ether at reduced pressure on a rotary evaporator. The residue when examined by gas chromatography is found to be 97-98 percent pure. Distillation of the residue gives 7.5 parts (63 percent) of 1,2-bis(difluoramino)ethyl methacrylate (b.p. 50° C/5.5 mm. of mercury), nD20 1.3944. Identification is based on infrared spectral data and elemental analysis. The product conforms to the known 1,2-bis(difluoramino)-ethyl methacrylate. The product gives the following analysis:

Sources & evidence

ORD record
ord-f3914206de9e4538877452030f8c07c1
Source dataset
uspto-grants-1976_07
Patent number
US03968150

Reaction notes

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