Reaction #6918

Reaction equation

2-amino-4-fluoro-5-iodo-benzoic acid

trichloromethylchloroformate

→

title compound

Yield 90.4%

4-Fluoro-5-iodo-isatoic anhydride

Yield 90.4%

Solvents

—

hexanes

dioxane

Conditions

Workup

1. 1
   Otherequipped with a magnetic stir bar
2. 2
   Temperaturereflux condenser
3. 3
   Temperatureheated
4. 4
   Temperatureto reflux for 16 hours
5. 5
   Temperatureto cool
6. 6
   FiltrationThe solid was collected by suction filtration
7. 7
   Washwashed with an additional 0.5 litres of hexanes
8. 8
   Otherdried under vacuum at room temperature

Procedure

Anhydrous dioxane (0.5 litres), 2-amino-4-fluoro-5-iodo-benzoic acid (46 grams, 164 mmoles), and trichloromethylchloroformate (97.4 grams, 492 mmoles) were added to a one litre one neck flask equipped with a magnetic stir bar and reflux condenser. The solution was placed under anhydrous nitrogen, stirred and heated to reflux for 16 hours. The reaction mixture was allowed to cool and was poured into one litre of hexanes. The solid was collected by suction filtration, washed with an additional 0.5 litres of hexanes, and dried under vacuum at room temperature to yield 45.5 grams (90%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ: 11.86(s, 1H), 8.24(d, 1H), 6.84(d, 1H). ESI-MS m/z 308 (M+1).

Source