Diethyl Carbonate → HCID 11358513, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.7 ml (14 mmol) of diethyl carbonate and 2.3 g (10 mmol) of 4-bromo-2,5-dimethylbenzoic acid in 15 ml tetrahydrofuran is added dropwise, over 2.5 hours, to a solution cooled to −78° C., prepared from 4.2 ml (30 mmol) of diisopropylamine and 19 ml of a 1.6 molar n-butyl lithium solution in hexane, in 35 ml tetrahydrofuran. Then it is heated to 0° C., poured into 200 ml of 3% NH4Cl solution, adjusted to pH 6 with acetic acid and extracted with ethyl acetate. The ethyl acetate phase is washed with 14% NaCl solution and dried with Na2SO4. The solvent is distilled off and the residue remaining is triturated several times in a little diisopropylether/petroleum ether and then dried.

Provenance & Evidence