Hydrochloric Acid → 5-Fluoro-2-iodobenzoic acid

Temperature

100 °C

The title compound was prepared from the following procedure described in Collection Czechoslov. Chem. Commun., vol. 40, p. 719 (1975). To an ice-cold mixture of 2-amino-5-fluorobenzoic acid (9.0 g, 58.0 mmol) and conc. hydrochloric acid (50 mL) was added dropwise a solution of sodium nitrite (4.42 g, 64.1 mmol) in water (10 mL). Subsequently, a solution of potassium iodide (14.5 g, 87.5 mmol) and conc. sulfuric acid (4 mL) in water (30 mL) was added at the same temperature, and the mixture was heated to 100° C. and stirred for 2 hours. After the solution was cooled to room temperature, the mixture was poured into an aqueous solution of sodium thiosulfate, and organic matter was extracted with ethyl acetate. The extract was washed with saturated brine and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give crude crystals. The crystals were collected by filtration, washed with hexane/diethylether, and air dried to give the title compound (6.33 g, 41% yield).

1. customThe title compound was prepared from the following procedure
2. customdescribed in Collection Czechoslov
3. temperatureAfter the solution was cooled to room temperature
4. extractionwas extracted with ethyl acetate
5. washThe extract was washed with saturated brine and water
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customto give crude crystals
9. filtrationThe crystals were collected by filtration
10. washwashed with hexane/diethylether, and air
11. customdried

ORD record

ord-8ebb34ae43f6472587d232c1e3da8f03

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06949648B2