Methanol → Methyl 3-hydroxy-4-iodobenzoate

3-Hydroxy-4-iodobenzoic acid (12.55 g, 47.5 mmol) is dissolved in MeOH (200 mL), treated slowly drop-wise with thionyl chloride (32.3 mL, 443 mmol) at RT, then heated to reflux for 20 h. The mixture is concentrated to dryness and partitioned between CH2Cl2 (100 mL) and saturated NaHCO3 (50 mL). Not all of the residue dissolves, so the mixture is filtered and the solid is washed with a small amount of CH2Cl2 in MeOH. The original filtrate and the organic washes are combined, concentrated to dryness, dissolved in 10% MeOH/CH2Cl2 (200 mL), diluted with water (50 mL) and the layers separated. The organics are washed with saturated NaHCO3 (2×50 mL), then water (50 mL), dried (Na2SO4) and concentrated to a tan solid. This solid is triturated with CH2Cl2 (50 mL) and filtered. The two solids are combined to afford 9.4 g (70%) of methyl 3-hydroxy-4-iodobenzoate as a beige solid. HRMS (FAB) calcd for C8H7IO3+H: 278.9520, found 278.9521 (M+H)+.

1. additiontreated slowly
2. temperatureheated
3. temperatureto reflux for 20 h
4. concentrationThe mixture is concentrated to dryness
5. custompartitioned between CH2Cl2 (100 mL) and saturated NaHCO3 (50 mL)
6. dissolutionNot all of the residue dissolves, so the mixture
7. filtrationis filtered
8. washthe solid is washed with a small amount of CH2Cl2 in MeOH
9. concentrationconcentrated to dryness
10. dissolutiondissolved in 10% MeOH/CH2Cl2 (200 mL)
11. additiondiluted with water (50 mL)
12. customthe layers separated
13. washThe organics are washed with saturated NaHCO3 (2×50 mL)
14. dry with materialwater (50 mL), dried (Na2SO4)
15. concentrationconcentrated to a tan solid
16. customThis solid is triturated with CH2Cl2 (50 mL)
17. filtrationfiltered

ORD record

ord-21bad1f8cafb46c38ac54852a9ce000a

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06894042B2