1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → Tert-butyl 2-fluoro-6-iodobenzoate

Participants

Reaction Steps

N,N-Dimethylformamide di-t-butyl acetal (3.8 ml, 3.2 g) was added to a stirred mixture of 2-fluoro-6-iodobenzoic acid (1.25 g) in toluene (25 ml). The mixture was then stirred at 90° for 4 h, allowed to stand at room temperature for 60 h before further dimethylformamide di-t-butyl acetal (1 ml, 0.85 g) was added and heating continued at 90° for 90 min. After cooling, the orange solution was washed with water (50 ml), brine (50 ml), 10% aqueous lithium chloride solution and 8% aqueous sodium bicarbonate solution (50 ml), dried and concentrated in vacuo-to afford an orange liquid (1.9 g). Purification by chromatography eluting with System A (1:1) gave the title compound (1.37 g) as an orange liquid.

Provenance & Evidence