Dimethylformamide → Methyl 3-iodo-5-nitrobenzoate

Participants

Reaction Steps

To a solution of 3-iodo-5-nitro-benzoic acid (5.88 g, 20.07 mmol) in dichloromethane (60 mL) at room temperature under nitrogen was added oxalyl chloride (1.92 mL, 24.28 mmol) and a drop of DMF. The mixture was stirred for 1 h. methanol (20 mL), DMAP (0.245 g, 2.00 mmol), and triethylamine (3.08 mL, 24.28 mmol) were added and the mixture was stirred for an additional 2 h. Water was added and the product was extracted, washed with water, then brine, dried over magnesium sulfate and concentrated to dryness. Purification by chromatography gave 6.04 g of 3-iodo-5-nitro-benzoic acid methyl ester, as a yellow solid.

Provenance & Evidence