Lithium iodide → 2,6-Dichloro-4-iodobenzoic acid

Temperature

130 °C

Methyl 2,6-dichloro-4-iodobenzoate (46 g, 0.14 mol) was dissolved in pyridine (1380 mL) and water (230 mL). Lithium iodide (37.2 g, 0.28 mol) was added in one portion. The resulting mixture was heated at 130° C. for 30 hours. The reaction was concentrated under reduced pressure. The residue was dissolved in 2N HCl (500 mL) and extracted with ethyl acetate (3×1 L). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in N-methyl morpholine (5 mL) and concentrated again. The residue was diluted with 2N HCl (100 mL) and extracted with dichloromethane (3×100 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give 2,6-dichloro-4-iodobenzoic acid (39 g, yield: 88%). 1H NMR (DMSO-d6, 400 MHz) δ 14.26 (brs, 1H), 7.99 (s, 2H).

1. concentrationThe reaction was concentrated under reduced pressure
2. dissolutionThe residue was dissolved in 2N HCl (500 mL)
3. extractionextracted with ethyl acetate (3×1 L)
4. dry with materialThe combined organic extracts were dried over Na2SO4
5. concentrationconcentrated under reduced pressure
6. dissolutionThe residue was dissolved in N-methyl morpholine (5 mL)
7. concentrationconcentrated again
8. additionThe residue was diluted with 2N HCl (100 mL)
9. extractionextracted with dichloromethane (3×100 mL)
10. dry with materialThe combined organic extracts were dried over Na2SO4
11. concentrationconcentrated under reduced pressure

ORD record

ord-a8263be9f1ce4fe78adda0017e1578b3

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08486950B2