Trifluoromethanesulfonic acid → 2-Chloro-5-iodo-4-methylbenzoic acid

To a solution of 4-methyl-2-chlorobenzoic acid 1 (2.50 g, 14.7 mmol) and (trifluoromethyl) sulfonic acid (65.0 mL, 73.3 mmol) in dichloromethane (20 mL) at 0° C. was added N-iodosuccinimide (3.50 g, 15.4 mmol) portion wise over a period of 10 minutes. The mixture was stirred at room temperature for 30 minutes, quenched with ice, then water (60 mL) and extracted into EtOAc (100 mL). The layers were separated and the aqueous layer was washed with EtOAc (2×50 mL). The combined organic layers were washed with 10% aqueous sodium sulfite solution (60 mL), dried over magnesium sulphate and concentrated in vacuo to afford the title compound (2.5 g, 57%).

1. customquenched with ice
2. extractionwater (60 mL) and extracted into EtOAc (100 mL)
3. customThe layers were separated
4. washthe aqueous layer was washed with EtOAc (2×50 mL)
5. washThe combined organic layers were washed with 10% aqueous sodium sulfite solution (60 mL)
6. dry with materialdried over magnesium sulphate
7. concentrationconcentrated in vacuo

ORD record

ord-abe93e6797474ae1b753b666d815bc38

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09328096B2