Diethyl Ether → Ethyl 2-ethoxy-4-iodobenzoate

Potassium carbonate (100 g, 724 mmol) and iodoethane (29.1 mL, 364 mmol) were added to a mechanically stirred solution of 2-hydroxy-4-iodobenzoic acid (16.0 g, 60.6 mmol, prepared according to Singh, S.; et al. J. Med. Chem. 1997, 40, 2472-2481) in 2-butanone (250 mL). The resulting mixture was heated at 80° C. for 16 h and then allowed to cool. Diethyl ether (250 mL) was added to the reaction vessel and the supernatant was transferred to a separatory funnel. Diethyl ether (250 mL) was again added to the reaction vessel to wash the remaining solid and the supernatant was again transferred to the separatory funnel. Water (400 mL) was added and the phases were separated. The aqueous phase was washed twice with diethyl ether (500 mL, 200 mL) and then the combined organic phases were washed with water (400 mL), brine (400 mL), dried over magnesium sulfate and concentrated. Purification of the crude residue by flash column chromatography (silica gel, eluting with 10% ethyl acetate in hexanes) gave ethyl 2-ethoxy-4-iodobenzoate as an off-white solid (9.50 g, 49%).

1. temperatureto cool
2. customthe supernatant was transferred to a separatory funnel
3. washto wash the remaining solid
4. additionWater (400 mL) was added
5. customthe phases were separated
6. washThe aqueous phase was washed twice with diethyl ether (500 mL, 200 mL)
7. washthe combined organic phases were washed with water (400 mL), brine (400 mL)
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated
10. customPurification of the crude residue
11. washby flash column chromatography (silica gel, eluting with 10% ethyl acetate in hexanes)

ORDレコード

ord-0c1fe54e63ef42f7a024b83713f18a34

出典データセット

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07579368B2