79158-36-4

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 3762-25-2 diethyl 4-methylbenzylphosphonate 
• 209626-93-7 (Fluoro-p-tolyl-trimethylsilanyl-methyl)-phosphonic acid diethyl ester 
• 79158-40-0 diethyl hydroxy(p-tolyl)methylphosphonate 

Downstream Products

• 79158-15-9 C₁₄H₂₆FO₃PSi₂ 
• 1181811-95-9 diethyl α,α-chlorofluoro-4-methylbenzylphosphonate 
• 79158-26-2 α-fluoro-4-methylbenzylphosphonic acid bis cyclohexylammonium salt 
• 79158-25-1 α-fluoro-4-methylbenzylphosphonic acid 

Relevant academic research and scientific papers

The first synthesis of diethyl α,α- chlorofluorobenzylphosphonates

Starting from a-hydroxyphosphonates, a wide variety of diethyl α,α-chlorofluorobenzylphosphonates have been obtained in pure form in a two-step procedure. The first step was chlorination of a- hydroxyphosphonates with Ph3P and CCl4,

Controlled monohalogenation of phosphonates: A new route to pure α- monohalogenated diethyl benzylphosphonates

Starting from diethyl benzylphosphonates, a wide variety of diethyl α- monofluoro, chloro, bromo and iodobenzylphosphonates have been obtained in pure form by a one-pot procedure. This high yielding method implies the intermediate protection of the benzyl anion with TMSCI followed by halogenation with an electrophilic halogenating reagent.

A highly selective synthesis of α-monofluoro- and α-monochloro- benzylphosphonates using eiectrophilic halogenation of benzylphosphonates carbanions

The selective electrophilic monofluorination and monochlorination of a wide variety of diethyl benzylphosphonates have been realized in a one-pot procedure. The monohalogenation was accomplished by intermediate of a benzylic carbanion protected with TMSCl

Synthesis of α- and γ-Fluoroalkylphosphonates

α-Fluorobenzylphosphonate esters are conventiently made by treating α-hydroxybenzylphosphonate esters with diethylaminosulphur trifluoride.The reaction is not subject to steric impedance and is extended to the α-fluorination of an α-hydroxybenzylphosphine oxide.For α-hydroxyallyl and α-hydroxycinnamylphosphonates, the replacement of the hydroxy group by fluorine proceeds via an SN2' rearrangement to give γ-fluoroalk-1-enylphosphonates exclusively.Dehydration rather than substitution occurs in the case of alcohols of secondary alkylphosphonates.

A Novel Synthesis of α- and γ-Fluoroalkylphosphonates

α-Hydroxybenzylphosphonate esters are efficiently converted into α-fluorobenzylphosphonate esters by diethylaminosulphur trifluoride while the corresponding α-hydroxyallyl- and α-hydroxycinnamylphosphonates undergo fluorination with allylic rearrangement;