Dimethylformamide → HCID 22601706, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-bromo-2,5-diiodo-4-methylthiophene (43 g, 100 mmol) in diethyl ether (300 mL) was treated with an etheral solution of 2.5 M butyllithium (40 mL, 100 mmol) during 5 min at −70 to −60° C. After 10 min, the mixture was treated with N,N-dimethylformamide (11 mL, 140 mmol) and the cooling bath was removed. Upon warming to 23° C., the mixture was quenched with 10% aqueous NH4Cl (500 mL) and extracted with ethyl acetate (3×500 mL). The combined extracts were washed with water and brine (500 mL each), dried (MgSO4) and concentrated in vacuo to give the crude product (31 g) as a rust-colored solid which was recrystallized from hot ethyl acetate. Vacuum filtration gave the title compound (25 g, 76%, m.p. 152-53° C.) as rust-colored needles.

Provenance & Evidence