Allyl bromide → Diethyl allylphosphonate

HRID 590892

Reaction equation

[CH2:1](Br)[CH:2]=[CH2:3].[CH2:5]([O:7][P:8]([O:12]CC)[O:9][CH2:10][CH3:11])[CH3:6]>>[CH2:1]([P:8](=[O:12])([O:9][CH2:10][CH3:11])[O:7][CH2:5][CH3:6])[CH:2]=[CH2:3]

Participants

Reactant 2

HCID 7841Allyl bromide

HCID 31215Triethyl phosphite

Product 1

HCID 573014Diethyl allylphosphonate

Procedure

Allyl bromide was treated with triethylphosphite in the absence of solvent using microwave conditions at 150° C. to give diethyl allylphosphonate. Diethyl allylphosphonate was combined with bromotrimethyl silane and subsequently quenched with methanol to afford diethyl allylphosphonic acid according to Scheme 7.

Workup

customat 150° C.

Sources & evidence

ORD record: ord-0e82b32ecb924645bc132c8becf71036
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09234985B2

Linked notes

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