Iodine → 4-Chloro-2-fluoro-6-iodobenzoic acid

Temperatur

100 °C

To a 250 mL flask were added 4-chloro-2-fluorobenzoic acid (4 g, 22.92 mmol), Pd(OAc)2 (0.257 g, 1.146 mmol), iodobenzene diacetate (8.12 g, 25.2 mmol), iodine (6.40 g, 25.2 mmol) and DMF (60 mL). The solution was heated under a nitrogen atmosphere at 100° C. for 20 h. LCMS showed about half of 4-chloro-2-fluorobenzoic acid was converted to the product (LCMS retention time 0.98 min, no MH+ peak). After cooling to room temperature, the solution was diluted with EtOAc and washed three times with 1 N HCl. The aqueous layers were combined and extracted once with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated to give a dark brown oil (16.4 g, 42% pure), which was taken to the next step without purification.

1. temperatureAfter cooling to room temperature
2. washwashed three times with 1 N HCl
3. extractionextracted once with EtOAc
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. customto give a dark brown oil (16.4 g, 42% pure), which
7. customwas taken to the next step without purification

ORD-Eintrag

ord-3f19965fe351414d9c0e744a7d758022

Quelldatensatz

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09242996B2