3-Bromotoluene → Diethyl (3-methylphenyl)phosphonate

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromotoluene (5 g) in tetrahydrofuran at −78° C. was added tert-butyllithium (35 ml of a 1.7 M solution in pentane). The mixture was stirred at −78° C. for 1 hour and diethl chlorophosphate (5.1 ml) was added. After 2 hours the mixture was warmed to 0° C., quenched with aqueous ammonium chloride and partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated. Purified by chromatography eluting with 40% ethyl acetate in isohexane. Yield 2.7 g.

Provenance & Evidence