Trifluoromethanesulfonic acid → 1-Fluoro-4-iodo-2-nitrobenzene

To a solution of 1-fluoro-2-nitrobenzene (5 g, 35.43 mmol) in triflic acid (15.6 ml, 177.15 mmol, 5 eq.) at 0° C. was added N-iodosuccinimide (9.57 g, 42.5 mmol, 1.2 eq.) portionwise and the mixture was stirred at RT for 1 h. The mixture was quenched by the addition of water and extracted with diethylether (3×150 ml). The combined organic layer was washed with water, aqueous sodium thiosulfate, brine and dried over sodium sulphate. The solvent was distilled off and the crude residue was purified by column chromatography (60-120 silica gel, 5% ethyl acetate in hexane) to afford the compound in 66% yield (6.2 g). 1H NMR (300 MHz, DMSO-d6): δ 8.42 (dd, 1H), 8.18-8.13 (m, 1H), 7.46-7.39 (m, 1H).

1. customThe mixture was quenched by the addition of water
2. extractionextracted with diethylether (3×150 ml)
3. washThe combined organic layer was washed with water, aqueous sodium thiosulfate, brine
4. dry with materialdried over sodium sulphate
5. distillationThe solvent was distilled off
6. customthe crude residue was purified by column chromatography (60-120 silica gel, 5% ethyl acetate in hexane)
7. customto afford the compound in 66% yield (6.2 g)

ORD record

ord-b17759ea87e94da1bf10aff5ae780223

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09447091B2