Iodoethane → 2-Chloro-3-ethoxy-5-iodophenol

Temperatur

60 °C

Iodoethane (0.78 mL, 9.6 mmol) and K2CO3 (1.3 g, 9.6 mmol) were added to a solution of 2-chloro-3-hydroxy-5-iodophenyl acetate (6) (2.0 g, 6.4 mmol) in DMF (5 mL) and the mixture was stirred at 60° C. for 1 h. The reaction mixture was cooled to RT, diluted with diethyl ether (100 mL) and washed with brine (3×100 mL). The solvent was removed in vacuo and the residue was dissolved in MeOH (20 mL). K2CO3 (1.0 g, 7.2 mmol) was added and the mixture was stirred at RT for 20 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc (100 mL) and water (100 mL). The organic layer was washed with water (100 mL) and evaporated in vacuo. The residue was purified by silica gel chromatography (40 g, 0-30% EtOAc in isohexane) to afford 2-chloro-3-ethoxy-5-iodophenol (7) (1.1 g, 58% yield) as a colourless solid: m/z 297 [M−H]− (ES−); 1H NMR (400 MHz, DMSO-d6) δ: 10.45 (1H, s), 6.89 (2H, d), 4.04 (2H, br s), 1.32 (3H, br s).

1. temperatureThe reaction mixture was cooled to RT
2. washwashed with brine (3×100 mL)
3. customThe solvent was removed in vacuo
4. dissolutionthe residue was dissolved in MeOH (20 mL)
5. stirringthe mixture was stirred at RT for 20 h
6. customThe solvent was removed in vacuo
7. customthe residue was partitioned between EtOAc (100 mL) and water (100 mL)
8. washThe organic layer was washed with water (100 mL)
9. customevaporated in vacuo
10. customThe residue was purified by silica gel chromatography (40 g, 0-30% EtOAc in isohexane)

ORD-Eintrag

ord-d513a6bb58c348e28669707b42ffd290

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09447028B2