DIETHYL (CHLOROMETHYL)PHOSPHONATE

Chemical Properties

Clear colorless to light yellow liquid

Uses

Reactant involved in:

• Subsequent alkylation after nucleophilic substitution
• One-pot alkylation-boration of α-haloalkylphosphonates
• Synthesis of cyclpentane and pyrrolidine derivatives via regioselective insertion reactions
• Phosphorylation leading to P-containing cyclopropanes
• Wadsworth-Emmons reactions
• Ring expansion of zircnacycles via carbenoid insertion

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 3799, 1987 DOI: 10.1016/S0040-4039(00)96387-1

reaction suitability

reaction type: C-C Bond Formation

Synthesis

Diethyl (chloromethyl)phosphonate is synthesized by a preparative scale of (EtO)2P(O)CH2Cl and other (1- chloroalkyl)phosphonates is relatively difficult. Ethanolysis of (chloromethyl)phosphonic dichloride is the most general and useful procedure (eq 1).