Methanol → Methyl 5-iodo-2,4-dimethylbenzoate

Temperatur

0 °C

5-Iodo-2,4-dimethylbenzoic acid (2.78 g, 10.1 mmol) obtained in Step 1 of Example 1-1 was placed in a reaction vessel, and then methanol (20 ml) was added thereto. The resulting mixture was cooled to 0° C. Thionyl chloride (2.2 ml, 30.1 mmol) was added dropwise to the mixture over about 10 minutes. The resulting mixture was stirred under reflux for 3 hours. The reaction solution was distilled off under reduced pressure. A saturated aqueous sodium bicarbonate solution was added to the obtained residue. The solution was extracted twice with ethyl acetate. The organic layers were combined together, and washed with a saturated aqueous sodium chloride solution. Then, the organic solution was dried over anhydrous magnesium sulfate. After removal of anhydrous magnesium sulfate by filtration, the liquid was washed with ethyl acetate. The filtrate and washing solution were combined together, and ethyl acetate was distilled off under reduced pressure to yield 2.85 g (97%) of 5-iodo-2,4-dimethylbenzoic acid methyl ester.

1. temperatureunder reflux for 3 hours
2. distillationThe reaction solution was distilled off under reduced pressure
3. additionA saturated aqueous sodium bicarbonate solution was added to the obtained residue
4. extractionThe solution was extracted twice with ethyl acetate
5. washwashed with a saturated aqueous sodium chloride solution
6. dry with materialThen, the organic solution was dried over anhydrous magnesium sulfate
7. customAfter removal of anhydrous magnesium sulfate
8. filtrationby filtration
9. washthe liquid was washed with ethyl acetate
10. washThe filtrate and washing solution
11. distillationethyl acetate was distilled off under reduced pressure

ORD-Eintrag

ord-2e8f504828f541ba87d5db13e373044d

Quelldatensatz

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08362236B2