Methanol → Methyl 4-chloro-3-iodobenzoate

A solution of 4-chloro-3-iodobenzoic acid (500 mg, 1.77 mmol, 1.00 equiv), methanol (20 mL), and concentrated sulfuric acid (0.35 g, 2.00 equiv) was heated to reflux overnight in an oil bath. The resulting mixture was concentrated in vacuo and diluted with 50 mL of ethyl acetate. The organic layer was washed with 3×20 mL of water and 3×20 mL of saturated aqueous sodium carbonate. The mixture was dried over anhydrous sodium sulfate and concentrated in vacuo, resulting in 0.52 g (99%) of methyl 4-chloro-3-iodobenzoate as a white solid.

1. temperatureto reflux overnight in an oil bath
2. concentrationThe resulting mixture was concentrated in vacuo
3. additiondiluted with 50 mL of ethyl acetate
4. washThe organic layer was washed with 3×20 mL of water and 3×20 mL of saturated aqueous sodium carbonate
5. dry with materialThe mixture was dried over anhydrous sodium sulfate
6. concentrationconcentrated in vacuo
7. customresulting in 0.52 g (99%) of methyl 4-chloro-3-iodobenzoate as a white solid

ORD record

ord-af6ae314b4aa4486bee584ea20654649

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012637B2