Diethyl Ether → HCID 18630385, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.5M LDA in THF (13 mL, 19.5 mmol) was added dropwise to an ether/liquid N2 cooled solution of N-ethyl 2,5-dichlorobenzamide (2.0 g, 9.2 mmol) and TMSCl (1.5 mL, 11.5 mmol) in THF (50 mL), maintaining the internal reaction temperature ≤-80° C. The resulting reaction mixture was stirred at -100° C. for 30 min, then was partitioned between ether and sat aq NaHCO3. The ether solution was dried (MgSO4), concentrated, and crystallized from EtOAc/hexanes to afford 1.15 g of the title compound as a white solid. m.p. 150°-153° C.

Provenance & Evidence